EP1565540B1 - Liquid crystalline compounds - Google Patents

Abstract

New liquid crystal compounds (I) containing cyclic structures, at least one of which is a tetrahydropyran-2,5-diyl group, and various linking groups, at least one of which is an oxydifluoromethylene group. Liquid crystal compounds of formula (I) are new: R1, R2 = H, halogen or optionally halogenated 1-15C alkyl or alkoxy (optionally with one or more CH2 groups replaced by -C triple bond C-, -CH=CH-, O, COO or OCO, with the proviso that one of these groups can also be CN, OCN, SCN, NCS or SF5; A1-A4 = trans-1,4-cyclohexylene (Cyc), 1,4-phenylene (Phe), 2- or 3-fluoro-1,4-phenylene, 3,5- or 2,3-difluoro-1,4-phenylene, 1,3-dioxan-5,2-diyl, tetrahydropyran-5,2-diyl or -2,5-diyl, dihydropyran-5,2-diyl, 1,4-cyclohex-4-enylene (optionally with F at position 5), or 1,4-bicyclo(2.2.2)octylene; Z1-Z3 = COO, OCO, CF2O, OCF2, CH2O, OCH2, -CH2CH2-, -(CH2)4-, -C2F4-, -CH2CF2-, -CF2CH2-, -CF=CF-, -CH=CH-, -C triple bond C- or a single bond; a, b, c = 0, 1, 2 or 3; and (a+b+c) = not more than 3. Independent claims are also included for: (1) liquid crystal compounds of formula (IA); (2) liquid crystal media containing at least two mesogenic compounds, which contain at least one compound (I); and (3) electro-optical liquid crystal displays containing such liquid crystal media. (a+b) = 1 or 2; and L1, L2 = H or F.

Description

The present invention relates to liquid-crystalline compounds and to a liquid-crystalline medium, the use thereof for electro-optical purposes and displays containing this medium.

Liquid crystals are mainly used as dielectrics in display devices, since the optical properties of such substances can be influenced by an applied voltage. Electro-optical devices based on liquid crystals are well known to the person skilled in the art and can be based on various effects. Such devices include, for example, dynamic scattering cells, DAP (out-of-phase deformation) cells, guest / host cells, twisted nematic (TN) cells, supertwisted nematic (STN) cells, SBE cells. Cells ("superbirefringence effect") and OMI cells ("optical mode interference"). The most common display devices are based on the Schadt-Helfrich effect and have a twisted nematic structure.

The liquid crystal materials must have good chemical and thermal stability and good stability against electric fields and electromagnetic radiation. Further, the liquid crystal materials should have low viscosity and provide short response times, low threshold voltages, and high contrast in the cells.

Furthermore, they should have a suitable mesophase at normal operating temperatures, ie in the widest possible range below and above room temperature, for example, for the above-mentioned cells a nematic or cholesteric mesophase. Since liquid crystals are generally used as mixtures of several components, it is important that the components are readily miscible with each other. Further properties, such as the electrical conductivity, the dielectric anisotropy and the optical anisotropy, must, depending on Cell type and application area meet different requirements. For example, materials for cells of twisted nematic structure should have positive dielectric anisotropy and low electrical conductivity.

For example, for matrix liquid crystal displays with integrated non-linear elements for single pixel switching (MFK displays), media with high positive dielectric anisotropy, broad nematic phases, relatively low birefringence, very high resistivity, good UV and temperature stability, and low vapor pressure are desired ,

1. 1. MOS (Metal Oxide Semiconductor) oder andere Dioden auf Silizium-Wafer als Substrat.
2. 2. Dünnfilm-Transistoren (TFT) auf einer Glasplatte als Substrat.

Such matrix liquid crystal displays are known. As non-linear elements for individual switching of the individual pixels, for example, active elements (ie transistors) can be used. One speaks then of an "active matrix", whereby one can distinguish two types:

1. 1. MOS (Metal Oxide Semiconductor) or other diodes on silicon wafer as a substrate.
2. 2. Thin-film transistors (TFT) on a glass plate as a substrate.

The use of monocrystalline silicon as a substrate material limits the display size, since the modular composition of various partial displays on the joints leads to problems.

In the more promising type 2, which is preferred, the TN effect is usually used as the electro-optical effect. A distinction is made between two technologies: TFTs made of compound semiconductors such as CdSe or TFTs based on polycrystalline or amorphous silicon. The latter technology is being worked on worldwide with great intensity.

The TFT matrix is applied on the inside of one glass plate of the display, while the other glass plate on the inside carries the transparent counter electrode. Compared to the size of the pixel electrode, the TFT is very small and practically does not disturb the image. This technology can also be extended to fully color-capable image representations, wherein a mosaic of red, green and blue filters is arranged such that each one filter element is opposite to a switchable image element.

The TFT displays usually operate as TN cells with crossed polarizers in transmission and are backlit.

The term MFK displays here includes any matrix display with integrated nonlinear elements, i. in addition to the active matrix also displays with passive elements such as varistors or diodes (MIM = metal-insulator-metal).

Such MFK displays are particularly suitable for TV applications (eg Taschenfemseher) or for high-information displays for computer applications (laptop) and in the automotive or aircraft. In addition to problems with regard to the angle dependence of the contrast and the switching times, difficulties arise with MFK displays due to the insufficiently high specific resistance of the liquid-crystal mixtures [ TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984 : A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, p. 141 ff, Paris; STROMER, M., Proc. Eurodisplay 84, Sept. 1984 : Design of Thin Film Transistors for Matrix Liquid Crystal Displays, p. 145 ff, par is]. With decreasing resistance, the contrast of a MFK display deteriorates and the problem of "after image elimination" may occur. Since the specific resistance of the liquid crystal mixture decreases by interaction with the inner surfaces of the display, generally over the lifetime of an MFK display, a high (initial) resistance is very high important to maintain acceptable service life. In particular, in low-volt mixtures, it has not been possible to realize very high resistivities. Furthermore, it is important that the resistivity shows the smallest possible increase with increasing temperature and after temperature and / or UV exposure. Also particularly disadvantageous are the low-temperature properties of the mixtures of the prior art. It is required that no crystallization and / or smectic phases occur even at low temperatures, and that the temperature dependence of the viscosity is as low as possible. The MFK displays from the prior art thus do not meet today's requirements.

Thus, there is still a great need for MFK displays with very high resistivity at the same time large working temperature range, short switching times even at low temperatures and low threshold voltage, which do not show these disadvantages or only to a lesser extent.

• erweiterter nematischer Phasenbereich (insbesondere zu tiefen Temperaturen)
• Schaltbarkeit bei extrem tiefen Temperaturen (out-door-use, Automobil, Avionik)
• erhöhte Beständigkeit gegenüber UV-Strahlung (längere Lebensdauer)

In TN (Schadt-Helfrich) cells, media are desired which allow the following advantages in the cells:

• extended nematic phase range (especially at low temperatures)
• Switchability at extremely low temperatures (out-door-use, automotive, avionics)
• increased resistance to UV radiation (longer life)

With the media available from the prior art, it is not possible to realize these advantages while maintaining the other parameters.

For higher-twisted cells (STN), media are desired which allow for higher multiplexability and / or lower threshold voltages and / or broader nematic phase ranges (especially at low temperatures). For this purpose, a further expansion of the available parameter space (clearing point, transition smectic-nematic or melting point, viscosity, dielectric values, elastic sizes) is urgently desired.

In the publication DE 10008712 A1 For example, liquid crystalline media having at least one compound comprising an oxa-cyclohexane ring and a -CF ₂ O group are disclosed. The publication EP 1182186 A2 discloses a process for preparing compounds having a CF ₂ O group between a cyclohexane ring and a benzene ring on the side of the O atom. Further substituents other rings are possible, including an oxa-cyclohexane-1,4-diyl. In the publication DE 10050071 A1 discloses a liquid crystal composition having compounds containing a 2,5-substituted tetrahydropyran ring.

The invention has for its object to provide media especially for such MFK, IPS, TN or STN displays that do not have the disadvantages mentioned above, or only to a lesser extent, and preferably at the same time very high resistivities and low threshold voltages. For this task, liquid-crystalline compounds are required which have a high clearing point and a low rotational viscosity.

It has now been found that this object can be achieved by using the liquid-crystalline compounds according to the invention.

worin

R¹ und R²

jeweils unabhängig voneinander H, Halogen, einen halogenierten oder unsubstituierten Alkyl- oder Alkoxyrest mit 1 bis 15 C-Atomen, wobei in diesen Resten auch eine oder mehrere CH₂-Gruppen jeweils unabhängig voneinander durch -C≡C-, -CH=CH-, -0-, -CO-O- oder -O-CO- so ersetzt sein können, dass O-Atome nicht direkt miteinander verknüpft sind, wobei einer der Reste R¹ und R² auch CN, OCN, SCN, NCS oder SF₅ bedeuten kann,

A¹, A², A³ und A⁴

jeweils unabhängig voneinander

Z¹, Z² und Z³

jeweils unabhängig voneinander -CO-O-, -O-CO-, -CF₂O-, -OCF_2-, -CH₂O_-, -OCH₂-, -CH₂CH₂-, -(CH₂)₄-, -C₂F₄-. -CH₂CF₂-, -CF₂CH₂-, -CF=CF-, -CH=CH-, -C≡C- oder eine Einfachbindung, und

a, b und c

jeweils unabhängig voneinander 0,1,2 oder 3, wobei a + b + c ≤ 3 ist,

bedeuten.The invention thus relates to liquid-crystalline compounds of the formula I,

wherein

R ¹ and R ²

each independently of one another H, halogen, a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where in these radicals also one or more CH ₂ groups are each independently denoted by -C≡C-, -CH = CH- , -O-, -CO-O- or -O-CO- can be replaced so that O atoms are not directly linked to each other, where one of the radicals R ¹ and R ² also CN, OCN, SCN, NCS or SF _{5 can} mean

A ¹ , A ² , A ³ and A ⁴

each independently

Z ¹ , Z ² and Z ³

are each independently -CO-O-, -O-CO-, -CF ₂ O-, -OCF _2-, -CH ₂ O _-, -OCH ₂ -, -CH ₂ CH ₂ -, - (CH _{2) 4} -, -C ₂ F ₄ -. -CH ₂ CF ₂ -, -CF ₂ CH ₂ -, -CF = CF-, -CH = CH-, -C≡C- or a single bond, and

a, b and c

independently of each other 0,1,2 or 3, where a + b + c ≤ 3,

mean.

The invention further relates to the use of the compounds of the formula I in liquid-crystalline media.

The compounds of the formula I have a wide range of applications. Depending on the choice of substituents, these compounds may serve as base materials from which liquid crystalline media are predominantly composed; However, it is also possible to add compounds of the formula I to liquid-crystalline base materials from other classes of compounds in order, for example, to influence the dielectric and / or optical anisotropy of such a dielectric and / or to optimize its threshold voltage and / or its viscosity.

The compounds of the formula I are colorless in the pure state and form liquid-crystalline mesophases in a temperature range which is favorably located for the electro-optical use. In particular, the compounds according to the invention are distinguished by their broad nematic phase range. In liquid-crystalline mixtures, the substances according to the invention suppress the smectic phases and lead to a marked improvement in the low-temperature storage stability. Chemically, thermally and against light, they are stable.

The invention relates in particular to the compounds of the formula I in which R ^{1 is} alkyl or alkenyl and R ^{2 is} halogen or OCF ₃ . Halogen is preferably F, furthermore CI.

A⁴ bedeutet insbesondere

Particular preference is given to compounds of the formula I in which a = 0, furthermore a = 1. Z ¹ , Z ² and / or Z ³ is preferably a single bond, furthermore -CF ₂ O- OCF ₂ -, -C ₂ F ₄ -, -CH ₂ O-, -OCH ₂ - or -COO-. A ¹ , A ² , A ³ and A ^{4 are} preferably

A ⁴ means in particular

worin a und b jeweils 0, 1 oder 2 und a + b = 1 oder 2 bedeuten. Vorzugsweise bedeutet a =1 und b = 0 oder a = 0 und b = 1. Vorzugsweise ist L¹ = F und L² = H oder Fluor, insbesondere bedeuten L¹ = L² = Fluor.Particular preference is given to compounds of the formulas IA

wherein a and b are each 0, 1 or 2 and a + b = 1 or 2. Preferably, a = 1 and b = 0 or a = 0 and b = 1. Preferably, L ¹ = F and L ² = H or fluorine, in particular L ¹ = L ² = fluorine.

R ¹ is preferably alkyl, alkoxy, alkenyl, alkenyloxy. Preferably, R ^{2 is} F, Cl, OCF ₃ , OCHF ₂ , OCHFCF ₃ , OCF ₂ CHFCF ₃ , CN, SF ₅ , NCS, SCN, in particular F or OCF ₃ , R ¹ is preferably straight-chain alkyl or alkenyl. L ¹ and L ^{2 are} each, independently of one another, H or F. Particular preference is given to compounds in which X = L ¹ = L ² = fluorine, furthermore X = OCF ₃ and L ¹ = L ² = F.

worin R¹ die oben angegebenen Bedeutungen hat X besitzt die Bedeutungen von R².Particularly preferred compounds of the formula I are the compounds of the formulas I1 to I31,

wherein R ¹ has the meanings given above X has the meanings of R ² .

The compounds of formula I can be very easily separated into the enantiomers, in which the racemate z. B. via a chiral HPLC column. The invention therefore relates to the compounds of the formula I which are present both as racemate and as enantiomer.

The compounds of the formula I are prepared by methods known per se, as described in the literature (for example in the standard works such as Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart), specifically under reaction conditions suitable for the said reactions are known and suitable. One can also make use of known per se, not mentioned here variants.

The compounds of the formula I can be prepared, for example, as follows:

The invention also provides electro-optical displays (in particular STN or MFK displays with two plane-parallel support plates, which form a cell with a border, integrated non-linear elements for switching individual pixels on the support plates and a nematic liquid crystal mixture in the cell with positive dielectric anisotropy and high resistivity) containing such media as well as the use of these media for electro-optical purposes.

The liquid-crystal mixtures according to the invention enable a significant expansion of the available parameter space.

The achievable combinations of clearing point, low temperature viscosity, thermal and UV stability, and dielectric anisotropy far surpass existing prior art materials.

The requirement for a high clearing point, nematic phase at low temperature and a high Δε has so far been insufficiently fulfilled. Liquid crystal mixtures, such as. Although MS 99295 (Merck KGaA, Darmstadt, Germany) have comparable clearing points and low-temperature stabilities, they have relatively high on-values as well as higher threshold voltages of about ≥ 1.7 V.

Other mixing systems have comparable viscosities and values of Δε, but have only clearing points in the region of 60 ° C.

The liquid-crystal mixtures according to the invention make it possible to maintain the nematic phase at -20 ° C. and preferably at -30 ° C., particularly preferably at -40 ° C., clearing points above 80 °, preferably above 90 °, particularly preferably above 100 ° C., simultaneously dielectric Anisotropy values △ ε ≥ 4, preferably ≥ 6 and to achieve a high value for the resistivity, whereby excellent STN and MKF displays can be achieved. In particular, the mixtures are characterized by low operating voltages. The TN thresholds are below 1.5 V, preferably below 1.3 V.

It is understood that by suitable choice of the components of the mixtures according to the invention also higher clearing points (eg above 110 °) can be realized at higher threshold voltage or lower clearing points at lower threshold voltages while maintaining the other advantageous properties. Likewise, mixtures can be obtained with a larger Δε and thus lower thresholds at correspondingly little increased viscosities. The MFK displays according to the invention preferably operate in the first transmission minimum according to Gooch and Tarry [ CH Gooch and HA Tarry, Electron. Lett. 10, 2-4, 1974 ; CH Gooch and HA Tarry, Appl. Phys., Vol. 8, 1575-1584, 1975 ], where in addition to particularly favorable electro-optical properties such as high slope of the characteristic and low angle dependence of the contrast ( DE-PS 30 22 818 ) at the same threshold voltage as in an analog display in the second minimum a smaller dielectric anisotropy is sufficient. As a result, significantly higher specific resistances can be achieved using the mixtures according to the invention in the first minimum than in the case of mixtures with cyano compounds. By suitable choice of the individual components and their proportions by weight, the person skilled in the art can set the birefringence required for a given layer thickness of the MFK display with simple routine methods.

The flow viscosity ν ₂₀ at 20 ° C is preferably <60 mm ² · s ^-1 , more preferably <50 mm ² · s ^-1 . The nematic phase range is preferably at least 90 °, in particular at least 100 °. Preferably, this range extends at least from -30 ° to + 80 °. The rotational viscosity γ ₁ at 20 ° C. is preferably <200 mPa · s, particularly preferably <180 mPa · s, in particular <160 mPa · s.

oder Ester der Formel

Measurements of the Capacity Holding Ratio (HR) [p. Matsumoto et al., Liquid Crystals 5 , 1320 (1989); K. Niwa et al., Proc. SID Conference, San Francisco, June 1984, p. 304 (1984); G. Weber et al., Liquid Crystals 5, 1381 (1989)] have shown that mixtures according to the invention comprising compounds of the formula I have a significantly smaller decrease in HR with increasing temperature than analogous mixtures instead of the compounds of formula I cyanophenylcyclohexanes of the formula

or esters of the formula

The UV stability of the mixtures according to the invention is significantly better, d. H. they show a much smaller decrease in HR under UV exposure.

Preferably, the media of the invention are based on several (preferably two, three or more) compounds of formula I, i. the proportion of these compounds is 5-95%, preferably 10-60%, and more preferably in the range of 15-40%.

The individual compounds of the formulas I to IX and their sub-formulas which can be used in the media according to the invention are either known or they can be prepared analogously to the known compounds.

• Das Medium enthält vorzugsweise ein, zwei oder drei homologe Verbindungen der Formel I, wobei jedes Homologe zu maximal 10 % in der Mischung enthalten ist.
• Medium enthält zusätzlich eine oder mehrere Verbindungen ausgewählt aus der Gruppe bestehend aus den allgemeinen Formeln II bis IX:
  
  
  
  
  
  
  
  

worin die einzelnen Reste die folgenden Bedeutungen haben:

R⁰

n-Alkyl, Oxaalkyl, Fluoralkyl, Alkenyloxy oder Alkenyl mit jeweils bis zu 9 C-Atomen

X⁰

F, Cl, halogeniertes Alkyl, halogeniertes Alkenyl, halogeniertes Alkenyloxy oder halogeniertes Alkoxy mit bis zu 7 C-Atomen,

Z°

-CH=CH-, -C₂H₄-, -(CH₂)₄-, -C₂F₄-, -CH₂O-, -OCH₂-, -CF=CF-, -CF₂O-, -OCF₂- oder -COO-,

Y1,Y2, Y³ und Y⁴

jeweils unabhängig voneinander H oder F, und

r

0 oder 1.

Preferred embodiments are given below:

• The medium preferably contains one, two or three homologous compounds of the formula I, wherein each homologue is contained in the mixture to a maximum of 10%.
• Medium additionally contains one or more compounds selected from the group consisting of the general formulas II to IX:
  
  
  
  
  
  
  
  

in which the individual radicals have the following meanings:

R ⁰

n-alkyl, oxaalkyl, fluoroalkyl, alkenyloxy or alkenyl, each having up to 9 carbon atoms

X ⁰

F, Cl, halogenated alkyl, halogenated alkenyl, halogenated alkenyloxy or halogenated alkoxy having up to 7 C atoms,

Z °

-CH = CH-, -C ₂ H ₄ -, - (CH ₂ ) ₄ -, -C ₂ F ₄ -, -CH ₂ O-, -OCH ₂ -, -CF = CF-, -CF ₂ O- , -OCF ₂ - or -COO-,

Y1, Y2, Y ³ and Y ⁴

each independently of one another H or F, and

r

0 or 1.

oder

• Das Medium enthält vorzugsweise eine oder mehrere Verbindungen der Formeln
  
  
  
  
  
  
  
  
  
  
  
  und/oder
  
  worin R⁰ und Y² die oben angegebene Bedeutung haben.
• Das Medium enthält vorzugsweise ein, zwei oder drei, ferner vier, Homologe der Verbindungen ausgewählt aus der Gruppe H1 bis H19 (n = 1-7):
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
• Das Medium enthält zusätzlich eine oder mehrere Verbindungen ausgewählt aus der Gruppe bestehend aus den allgemeinen Formeln X bis XV:
  
  
  
  
  
  
  worin R⁰, X⁰, Y¹, Y², Y³ und Y⁴ jeweils unabhängig voneinander eine der in Anspruch 8 angegebene Bedeutung haben. Vorzugsweise bedeutet X⁰ F, Cl, CF₃, OCF₃, OCHF₂. R⁰ bedeutet vorzugsweise Alkyl, Oxaalkyl, Fluoralkyl, Alkenyl oder Alkenyloxy.
• Der Anteil an Verbindungen der Formeln I bis IX zusammen beträgt im Gesamtgemisch mindestens 50 Gew.-%.
• Der Anteil an Verbindungen der Formel I beträgt im Gesamtgemisch 5 bis 50 Gew.-%.
• Der Anteil an Verbindungen der Formel II beträgt im Gesamtgemisch 3-40 Gew.-%.
• Der Anteil an Verbindungen der Formeln II bis IX im Gesamtgemisch beträgt 30 bis 70 Gew.-%.
  
  ist vorzugsweise
  
  
  
  
  
• Das Medium enthält Verbindungen der Formeln II, III, IV, V, VI, VII, VIII und/oder IX.
• R⁰ ist geradkettiges Alkyl oder Alkenyl mit 2 bis 7 C-Atomen.
• Das Medium besteht im wesentlichen aus Verbindungen der Formeln I bis XV.
• Das Medium enthält 5-40 Gew.-% an Verbindungen der Formeln H17 und/oder H18.
• Das Medium enthält weitere Verbindungen, vorzugsweise ausgewählt aus der folgenden Gruppe bestehend aus den allgemeinen Formeln XVI bis XX:
  
  
  
  
  

worin R⁰ und X⁰ die oben angegebene Bedeutung haben und die 1,4-Phenylenringe durch CN, Chlor oder Fluor substituiert sein können. Vorzugsweise sind die 1,4-Phenylenringe ein- oder mehrfach durch Fluoratome substituiert.

• Das Medium enthält weitere Verbindungen, vorzugsweise ausgewählt aus der folgenden Gruppe bestehend aus den Formeln RI bis RIX,
  
  
  
  
  
  
  
  
  
  worin

  R⁰

  n-Alkyl, Oxaalkyl, Fluoralkyl, Alkenyloxy oder Alkenyl mit jeweils bis zu 9 C-Atomen,

  d

  0, 1 oder 2,

  Y¹

  H oder F,

  Alkyl oder Alkyl*

  jeweils unabhängig voneinander ein geradkettiger oder verzweigter Alkylrest mit 1-9 C-Atomen,

  Alkenyl oder Alkenyl*

  jeweils unabhängig voneinander einen geradkettigen oder verzweigten Alkenylrest mit bis zu 9 C-Atomen

  bedeuten.
• Das Medium enthält vorzugsweise eine oder mehrere Verbindungen der Formeln
  
  
  
  
  
  
  
  
  worin n und m jeweils eine ganze Zahl von 1-9 bedeuten.
• Das Gewichtsverhältnis I: (II + III + IV + V + VI + VII + VIII + IX) ist vorzugsweise 1 : 10 bis 10 : 1.
• Das Medium besteht im wesentlichen aus Verbindungen ausgewählt aus der Gruppe bestehend aus den allgemeinen Formeln I bis XV.

The compound of formula IV is preferred

or

• The medium preferably contains one or more compounds of the formulas
  
  
  
  
  
  
  
  
  
  
  
  and or
  
  wherein R ⁰ and Y ^{2 have} the meaning given above.
• The medium preferably contains one, two or three, further four, homologues of the compounds selected from the group H1 to H19 (n = 1-7):
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
• The medium additionally contains one or more compounds selected from the group consisting of the general formulas X to XV:
  
  
  
  
  
  
  wherein R ⁰ , X ⁰ , Y ¹ , Y ² , Y ³ and Y ⁴ each independently have one of the meanings given in claim 8. Preferably, X ^{0 is} F, Cl, CF ₃ , OCF ₃ , OCHF ₂ . R ⁰ is preferably alkyl, oxaalkyl, fluoroalkyl, alkenyl or alkenyloxy.
• The proportion of compounds of the formulas I to IX together in the total mixture is at least 50% by weight.
• The proportion of compounds of formula I is in the total mixture 5 to 50 wt .-%.
• The proportion of compounds of formula II is in the total mixture 3-40 wt .-%.
• The proportion of compounds of the formulas II to IX in the total mixture is 30 to 70 wt .-%.
  
  is preferable
  
  
  
  
  
• The medium contains compounds of the formulas II, III, IV, V, VI, VII, VIII and / or IX.
• R ⁰ is straight-chain alkyl or alkenyl having 2 to 7 C atoms.
• The medium consists essentially of compounds of formulas I to XV.
• The medium contains 5-40% by weight of compounds of the formulas H17 and / or H18.
• The medium contains further compounds, preferably selected from the following group consisting of the general formulas XVI to XX:
  
  
  
  
  

wherein R ⁰ and X ^{0 have} the abovementioned meaning and the 1,4-phenylene rings may be substituted by CN, chlorine or fluorine. Preferably, the 1,4-phenylene rings are mono- or polysubstituted by fluorine atoms.

• The medium contains further compounds, preferably selected from the following group consisting of the formulas RI to RIX,
  
  
  
  
  
  
  
  
  
  wherein

  R ⁰

  n-alkyl, oxaalkyl, fluoroalkyl, alkenyloxy or alkenyl having in each case up to 9 C atoms,

  d

  0, 1 or 2,

  Y ¹

  H or F,

  Alkyl or alkyl *

  each independently of one another a straight-chain or branched alkyl radical having 1-9 C atoms,

  Alkenyl or alkenyl *

  each independently of one another a straight-chain or branched alkenyl radical having up to 9 C atoms

  mean.
• The medium preferably contains one or more compounds of the formulas
  
  
  
  
  
  
  
  
  wherein n and m each represents an integer of 1-9.
• The weight ratio I: (II + III + IV + V + VI + VII + VIII + IX) is preferably 1:10 to 10: 1.
• The medium consists essentially of compounds selected from the group consisting of the general formulas I to XV.

It has been found that even a relatively small proportion of compounds of the formula I in admixture with conventional liquid crystal materials, but in particular with one or more compounds of the formula II, III, IV, V, VI, VII, VIII or IX to a considerable reduction of Threshold voltage and too low values for the birefringence results, while simultaneously observing broad nematic phases with low transition temperatures smectic-nematic, whereby the storage stability is improved. The compounds of formulas I to IX are colorless, stable and readily miscible with each other and with other liquid crystal materials.

The term "alkyl" or "alkyl *" embraces straight-chain and branched alkyl groups having 1-9 carbon atoms, in particular the straight-chain groups methyl, ethyl, propyl, butyl, pentyl, hexyl and heptyl. Groups of 2-5 carbon atoms are generally preferred.

The term "alkenyl" or "alkenyl *" includes straight-chain and branched alkenyl groups having up to 9 carbon atoms, especially the straight-chain groups. Particularly preferred alkenyl groups are C ₂ - C ₇ - 1E-alkenyl, C ₄ -C ₇ -3E-alkenyl, C ₅ -C ₇ -4-alkenyl, C ₆ -C ₇ -5-alkenyl and C ₇ -6-alkenyl , in particular C ₂ C ₇ -1 E-alkenyl, C ₄ -C ₇ 3E-alkenyl and C ₅ -C ₇ -4-alkenyl. Examples of preferred alkenyl groups are vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl , 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl, 6-heptenyl and the like. Groups of up to 5 carbon atoms are generally preferred.

The term "fluoroalkyl" preferably includes straight-chain fluoro-end-capped groups, ie, fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, and 7-fluoroheptyl. Other positions of the fluorine are not excluded.

The term "oxaalkyl" preferably includes straight-chain radicals of the formula C _n H _{2n + 1} -O- (CH ₂ ) _m , wherein n and m are each independently 1 to 6. Preferably, n = 1 and m is 1 to 6.

By suitably selecting the meanings of R ⁰ and X ⁰ , the response times, the threshold voltage, the transconductance of the transmission characteristics etc. can be modified in the desired manner. For example, 1E-alkenyl radicals, 3E-alkenyl radicals, 2E-alkenyloxy radicals and the like generally lead to shorter response times, improved nematic tendencies and a higher ratio of the elastic constants k ₃₃ (bend) and k ₁₁ (splay) compared to alkyl or alkoxy. 4-Alkenyl radicals, 3-alkenyl radicals and the like generally give lower threshold voltages and smaller values of k ₃₃ / k ₁₁ compared to alkyl and alkoxy radicals.

A group -CH ₂ CH ₂ - in Z ¹ and / or Z ² generally results in higher values of k ₃₃ / k ₁₁ compared to a single covalent bond. Higher values of k ₃₃ / k ₁₁ allow, for example, flatter transmission characteristics in TN cells with 90 ° twist (to achieve shades of gray) and steeper transmission characteristics in STN, SBE and OMI cells (higher multiplexability) and vice versa.

The optimum ratio of the compounds of the formulas I and II + III + IV + V + VI + VII + VII + VIII + IX depends largely on the desired properties, on the choice of the components of the formulas I, II, III, IV, V, VI, VII, VIII and / or IX and from the choice of other optionally present components. Suitable proportions within the range given above can be easily determined on a case-by-case basis.

The total amount of compounds of the formulas I to XV in the mixtures according to the invention is not critical. The mixtures may therefore contain one or more other components to optimize various properties. However, the observed effect on the response times and the threshold voltage is generally greater the higher the total concentration of compounds of the formulas I to XV.

In a particularly preferred embodiment, the media according to the invention comprise compounds of the formulas II to IX (preferably II and / or III) wherein X is ⁰ OCF _3, OCHF _2, F, OCH = CF _2, OCF = CF _2, OCF ₂ CHFCF _3, or OCF ₂ -CF ₂ H means. A favorable synergistic effect with the compounds of the formula I leads to particularly advantageous properties.

The structure of the MFK display of polarizers, electrode base plates and electrodes with surface treatment according to the invention corresponds to the usual construction for such displays. Here, the term of the usual construction is broad and includes all modifications and modifications of the MFK display, in particular matrix display elements based on poly-Si TFT or MIM.

However, a significant difference of the displays of the invention on the basis of the usual twisted nematic cell is the choice of the liquid crystal parameters of the liquid crystal layer.

The preparation of the liquid crystal mixtures which can be used according to the invention is carried out in a conventional manner. In general, the desired amount of the components used in lesser amount is dissolved in the constituent of the main component, expediently at elevated temperature. It is also possible to use solutions of the components in an organic solvent, e.g. in acetone, chloroform or methanol, and to remove the solvent again after thorough mixing, for example by distillation.

The dielectrics may also other, known in the art and described in the literature additives such. As stabilizers, antioxidation included. For example, 0-15% pleochroic dyes or chiral dopants may be added.

C means a crystalline, S a smectic, S _C a smectic C, S _B a smectic B, N a nematic and I the isotropic phase.

V ₁₀ denotes the voltage for 10% transmission (viewing direction perpendicular to the plate surface). t _on denotes the switch-on time and t _off the switch-off time at an operating voltage corresponding to twice the value of V ₁₀ . Δn denotes the optical anisotropy and n _o the refractive index. Δε denotes the dielectric anisotropy (Δε = ε _|| - ε _⊥ , where ε _{ll means} the dielectric constant parallel to the _longitudinal molecular _axes and ε _⊥ the dielectric constant perpendicular to it). The electro-optical data were measured in a TN cell in the 1st minimum (ie at a d · Δn value of 0.5 microns) at 20 ° C, unless expressly stated otherwise. The optical data were measured at 20 ° C unless expressly stated otherwise.

In the present application and in the following examples, the structures of the liquid crystal compounds are indicated by acronyms, wherein the transformation into chemical formulas according to following Tables A and B takes place. All radicals C _n H _{2n + 1} and C _m H _{2m + 1} are straight-chain alkyl radicals with n or m C atoms. n and m are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15. The coding according to Table B is self-evident. In Table A only the acronym for the main body is given. In the individual case, a code for the substituents R ¹ , R ² , L ¹ and L ² follows separately from the acronym for the main body with a dash: Code for R ¹ , R ² , L ¹ , L ² R ¹ R ² L ¹ L ² nm C _n H _{2n + 1} C _m H _{2m + 1} H H n Om C _n H _{2n + 1} OC _m H _{2m + 1} H H nO.m OC _n H _{2n + 1} C _m H _{2m + 1} H H n C _n H _{2n + 1} CN H H nN.F C _n H _{2n + 1} CN H F nF C _n H _{2n + 1} F H H nOF OC _n H _{2n + 1} F H. H n Cl C _n H _{2n + 1} Cl H H nF.F C _n H _{2n + 1} F H F nF.FF C _n H _{2n + 1} F F F nCF ₃ C _n H _{2n + 1} CF ₃ H H nOCF ₃ C _n H _{2n + 1} OCF ₃ H H nOCF ₃ .F C _n H _{2n + 1} OCF ₃ H F nOCF ₂ C _n H _{2n + 1} OCHF ₂ H H nS C _n H _{2n + 1} NCS H H RVSN C _r H _{2r + 1} -CH = CH-C _s H _2s - CN H H rESn C _r H _{2r + 1} -OC ₂ H _2s - CN H H nAm C _n H _{2n + 1} COOC _m H _{2m + 1} H H nOCCF ₂ .FF C _n H _{2n + 1} OCH ₂ CF ₂ H F F

Tabelle B:

Tabelle C: In der Tabelle C werden mögliche Dotierstoffe angegeben, die in der Regel den erfindungsgemäßen Mischungen in Mengen von 0,1 bis 10 Gew.% zugesetzt werden.

Tabelle D Stabilisatoren, die beispielsweise den erfindungsgemäßen Mischungen zugesetzt werden können, werden nachfolgend genannt.

Preferred mixture components are given in Tables A and B. <b><u> Table A: </ u></b>

In Table C possible dopants are given, which are usually added to the mixtures according to the invention in amounts of 0.1 to 10 wt.%.

Stabilizers which can be added, for example, to the mixtures according to the invention are mentioned below.

The following examples are intended to illustrate the invention without limiting it. Above and below, percentages are by weight. All temperatures are in degrees Celsius. Mp means melting point, bp. Clearing point. Furthermore, K = crystalline state, N = nematic phase, S = smectic phase and I = isotropic phase. The data between these symbols represent the transition temperatures. Δn means optical anisotropy (589 nm, 20 ° C.), Δε the dielectric anisotropy 1 kHz, 20 ° C.), the flow viscosity ν ₂₀ (mm ² / sec) was determined at 20 ° C. , The rotational viscosity γ ₁ (mPa · s) was also determined at 20 ° C.

"Conventional work-up" means: water is optionally added, extracted with dichloromethane, diethyl ether, methyl tert-butyl ether or toluene, separated, the organic phase is dried, evaporated and the product is purified by distillation under reduced pressure or crystallization and / or chromatography. The following abbreviations are used: n-BuLi 1.6 molar solution of n-butyllithium in n-hexane DMAP 4- (dimethylamino) pyridine THF tetrahydrofuran DCC N, N'-dicyclohexylcarbodiimide LDA lithium dimethylamide RT room temperature

example 1

Step 1.1

The preparation of B is carried out analogously to reference a) R. Baker, AL Boyes, CJ Swain, J. Chem. Soc. Perkin Trans. 1, 1990, 1415-1421 ; b) H. Hagiwara, T. Okabe, H. Ono, VP Kamat. T. Hoshi, T. Suzuku, M. Ando, J. Chem. Soc. Perkin Trans. 1, 2002, 895-900 ,

Step 1.2

A solution of 207 mmol 1,4-dibromobenzene in 250 ml diethyl ether is added dropwise at -50 ° C with 207 mmol BuLi (15% in hexane). Then added dropwise to a solution of 170 mmol B in 50 ml of diethyl ether at the same temperature, stirred for 30 min, allowed to come to 0 ° C and worked up as usual on water. The crude product (51 g) is dissolved in 400 ml of CH ₂ Cl ₂ and treated at -75 ° C with 400 mmol of triethylsilane. 400 mmol of boron trifluoride etherate are added dropwise, during which the temperature must not rise above -70.degree. Then allowed to come to -10 ° C, hydrolyzed with sat. NaHCO ₃ solution and worked up as usual aqueous. The crude product contains the trans / cis isomers in a ratio of 9: 1. It is crystallized from pentane at -20 ° C microns.

Step 1.3

73 mmol C are dissolved in 200 ml THF and cooled to -70 ° C. 73 mmol of BuLi (15% in hexane) are added dropwise first, followed by 73 mmol of trimethyl borate in 50 ml of THF. It is allowed to come to -20 ° C, adjusted to pH = 2 by addition of 2N HCl and worked up in water: The crude product is digested with hot heptane and crystallized at 0 ° C.

Step 1.4

A mixture of 60 mmol D , 300 ml of toluene, 120 mmol of NaOH, 50 ml of water and 30 ml of 30% H ₂ O ₂ is stirred at 45 ° C for 2 h. The mixture is adjusted to pH = 2 with 10% HCl and worked up with water. The crude product is recrystallized from heptane.

Step 1.5

22 mmol E are hydrogenated in 100 ml of xylene in the presence of 1.5 g of water wet 5% Pd-C catalyst at 5 bar and 130 ° C for 27.5 h. The work-up is done as usual. A colorless oil is obtained.

Step 1.6

A solution of 17 mmol of 2-trimethylsilyl-1,3-dithiane in 75 ml of THF is added at -70 ° C with 17 mmol BuLi (15% in hexane). The mixture is allowed to come to 0 ° C within 4 h, then cooled again to -70 ° C and added dropwise 17 mmol F in 25 ml of THF, allowed to come to room temperature, stirred for 18 h and worked up as usual aqueous. The crude product is crystallized from heptane. This gives colorless crystals.

Step 1.7

A solution of 6.12 mmol G in 50 ml CH ₂ Cl ₂ is added dropwise at -20 ° C with 6.27 mmol trifluoromethanesulfonic acid. It is allowed to come to room temperature for 30 minutes and then cooled to -70 ° C. Now, first a solution of 9.1 mmol 3,4,5-trifluorophenol and 10.1 mmol of triethylamine in 20l CH ₂ Cl ₂ , 5 min later added 31 mmol triethylamine tris (hydrofluoride). After a further 5 minutes, a suspension of 31.5 mmol of DBH (1,3-dibromo-5,5-dimethylhydanthoin) is added in small portions and stirring is continued for 1 h at -70 ° C. It is allowed to come to -10 ° C and the reaction mixture is poured into 400 ml of ice-cold NaOH. It works as usual on aqueous and purified the crude product by chromatography on silica gel (heptane / toluene 3: 2) and crystallization from pentane at -70 ° C. Colorless crystals are obtained: K 35 N 66.3 I; Δn = 0.0570; Δε = 13.4

hergestellt: R¹ X L¹ L² H F H H CH₃ F H H C₂H₅ F H H n-C₄H₉ F H H n-C₅H₁₁ F H H n-C₆H₁₃ F H H H F F H CH₃ F F H C₂H₅ F F H n-C₃H₇ F F H K 41 S_B 51 N 95,9 I; Δε = 9,7; Δn = 0,0688 n-C₄H₉ F F H K 31 S_B 64 N 97,1 I; Δε = 9,3; Δn = 0,0621 n-C₅H₁₁ F F H n-C₆H₁₃ F F H H F F F CH₃ F F F K 54 I, Δε = 14,8; △n = 0,0490 C₂H₅ F F F K 48 N (34,7) I; △ε = 14,1; △n = 0,054.0 n-C₃H₇ F F F n-C₄H₉ F F F K 43 N 66,1 I, △ε = 13,3; △n = 0,0590 n-C₅H₁₁ F F F K 39 N 75,3 I; Δε =11,8; △n = 0,0568 n-C₆H₁₃ F F F H Cl H H CH₃ Cl H H C₂H₅ Cl H H n-C₃H₇ Cl H H n-C₄H₉ Cl H H n-C₅H₁₁ Cl H H n-C₆H₁₃ Cl H H H Cl F H CH₃ Cl F H C₂H₅ Cl F H n-C₃H₇ Cl F H n-C₄H₉ Cl F H n-C₅H₁₁ Cl F H n-C₆H₁₃ Cl F H H Cl F F CH₃ Cl F F C₂H₅ Cl F F n-C₃H₇ Cl F F n-C₄H₉ Cl F F n-C₅H₁₁ Cl F F n-C₆H₁₃ Cl F F H OCF₃ H H CH₃ OCF₃ H H C₂H₅ OCF₃ H H n-C₃H₇ OCF₃ H H K -41 S_B 123 N 129,3 I; Δε = 9,1; Δn = 0,0780 n-C₄H₉ OCF₃ H H KC -54 S_B 129 I; Δε = 9,1; An = 0,0689 n-C₅H₁₁ OCF₃ H H n-C₆H₁₃ OCF₃ H H H OCF₃ F H CH₃ OCF₃ F H C₂H₅ OCF₃ F H n-C₃H₇ OCF₃ F H S_B 74 N 105,8 I; Δε = 11,7; Δn = 0,0701 n-C₄H₉ OCF₃ F H S_B 81 N 105,8 I; Δε =11,5; Δn = 0,0623 n-C₅H₁₁ OCF₃ F H n-C₆H₁₃ OCF₃ F H H OCF₃ F F CH₃ OCF₃ F F C₂H₅ OCF₃ F F n-C₃H₇ OCF₃ F F n-C₄H₉ OCF₃ F F n-C₅H₁₁ OCF₃ F F n-C₆H₁₃ OCF₃ F F H OCHF₂ H H CH₃ OCHF₂ H H C₂H₅ OCHF₂ H H n-C₃H₇ OCHF₂ H H n-C₄H₉ OCHF₂ H H n-C₅H₁₁ OCHF₂ H H n-C₆H₁₃ OCHF₂ H H H OCHF₂ F H CH₃ OCHF₂ F H C₂H₅ OCHF₂ F H n-C₃H₇ OCHF₂ F H n-C₄H₉ OCHF₂ F H n-C₅H₁₁ OCHF₂ F H n-C₆H₁₃ OCHF₂ F H H OCHF₂ F F CH₃ OCHF₂ F F C₂H₅ OCHF₂ F F n-C₃H₇ OCHF₂ F F n-C₄H₉ OCHF₂ F F n-C₅H₁₁ OCHF₂ F F n-C₆H₁₃ OCHF₂ F F H OCHFCF₃ H H CH₃ OCHFCF₃ H H C₂H₅ OCHFCF₃ H H n-C₃H₇ OCHFCF₃ H H n-C₄H₉ OCHFCF₃ H H n-C₅H₁₁ OCHFCF₃ H H n-C₅H₁₃ OCHFCF₃ H H H OCHFCF₃ F H CH₃ OCHFCF₃ F H C₂H₅ OCHFCF₃ F H n-C₃H₇ OCHFCF₃ F H n-C₄H₉ OCHFCF₃ F H n-C₅H₁₁ OCHFCF₃ F H n-C₆H₁₃ OCHFCF₃ F H H OCHFCF3 F F CH₃ OCHFCF₃ F F C₂H₅ OCHFCF₃ F F n-C₃H₇ OCHFCF₃ F F n-C₄H₉ OCHFCF₃ F F n-C₅H₁₁ OCHFCF₃ F F n-C₆H₁₃ OCHFCF₃ F F H OCHFCF₃ H H CH₃ OCHFCF₃ H H C₂H₅ OCHFCF₃ H H n-C₃H₇ OCHFCF₃ H H n-C₄H₉ OCHFCF₃ H H n-C₅H₁₁ OCHFCF₃ H H n-C₆H₁₃ OCHFCF₃ H H H OCHFCF₃ F H CH₃ OCHFCF₃ F H C₂H₅ OCHFCF₃ F H n-C₃H₇ OCHFCF₃ F H n-C₄H₉ OCHFCF₃ F H n-C₅H₁₁ OCHFCF₃ F H n-C₆H₁₃ OCHFCF₃ F H H OCHFCF₃ F F CH₃ OCHFCF₃ F F C₂H₅ OCHFCF₃ F F n-C₃H₇ OCHFCF₃ F F n-C₄H₉ OCHFCF₃ F F n-C₅H₁₁ OCHFCF₃ F F n-C₆H₁₃ OCHFCF₃ F F H OCF₂CHFCF₃ H H CH₃ OCF₂CHFCF₃ H H C₂H₅ OCF₂CHFCF₃ H H n-C₃H₇ OCF₂CHFCF₃ H H n-C₄H₉ OCF₂CHFCF₃ H H n-C₅H₁₁ OCF₂CHFCF₃ H H n-C₆H₁₃ OCF₂CHFCF₃ H H H OCF₂CHFCF₃ F H CH₃ OCF₂CHFCF₃ F H C₂H₅ OCF₂CHFCF₃ F H n-C₃H₇ OCF₂CHFCF₃ F H n-C₄H₉ OCF₂CHFCF3 F H n-C₅H₁₁ OCF₂CHFCF₃ F H n-C₆H₁₃ OCF₂CHFCF₃ F H H OCF₂CHFCF₃ F F CH₃ OCF₂CHFCF₃ F F C₂H₅ OCF₂CHFCF₃ F F n-C₃H₇ OCF₂CHFCF₃ F F n-C₄H₉ OCF₂CHFCF₃ F F n-C₅H₁₁ OCF₂CHFCF₃ F F n-C₆H₁₃ OCF₂CHFCF₃ F F H NCS H H CH₃ NCS H H C₂H₅ NCS H H n-C₃H₇ NCS H H n-C₄H₉ NCS H H n-C₅H₁₁ NCS H H n-C₆H₁₃ NCS H H H NCS F H CH₃ NCS F H C₂H₅ NCS F H n-C₃H₇ NCS F H n-C₄H₉ NCS F H n-C₅H₁₁ NCS F H n-C₆H₁₃ NCS F H H NCS F F CH₃ NCS F F C₂H₅ NCS F F n-C₃H₇ NCS F F n-C₄H₉ NCS F F n-C₅H₁₁ NCS F F n-C₆H₁₃ NCS F F H C₂F₅ H H CH₃ C₂F₅ H H C₂H₅ C₂F₅ H H n-C₃H₇ C₂F₅ H H n-C₄H₉ C₂F₅ H H n-C₅H₁₁ C₂F₅ H H n-C₆H₁₃ C₂F₅ H H H C₂F₅ F H CH₃ C₂F₅ F H C₂H₅ C₂F₅ F H n-C₃H₇ C₂F₅ F H n-C₄H₉ C₂F₅ F H n-C₅H₁₁ C₂F₅ F H n-C₆H₁₃ C₂F₅ F H H C₂F₅ F F CH₃ C₂F₅ F F C₂H₅ C₂F₅ F F n-C₃H₇ C₂F₅ F F n-C₄H₉ C₂F₅ F F n-C₅H₁₁ C₂F₅ F F n-C₆H₁₃ C₂F₅ F F H C₃F₇ H H CH₃ C₃F₇ H H C₂H₅ C₃F₇ H H n-C₃H₇ C₃F₇ H H n-C₄H₉ C₃F₇ H H n-C₅H₁₁ C₃F₇ H H n-C₆H₁₃ C₃F₇ H H H C₃F₇ F H CH₃ C₃F₇ F H C₂H₅ C₃F₇ F H n-C₃H₇ C₃F₇ F H n-C₄H₉ C₃F₇ F H n-C₅H₁₁ C₃F₇ F H n-C₆H₁₃ C₃F₇ F H H C₃F₇ F F CH₃ C₃F₇ F F C₂H₅ C₃F₇ F F n-C₃H₇ C₃F₇ F F n-C₄H₉ C₃F₇ F F n-C₅H₁₁ C₃F₇ F F n-C₆H₁₃ C₃F₇ F F H SF₅ H H CH₃ SF₅ H H C₂H₅ SF₅ H H n-C₃H₇ SF₅ H H n-C₄H₉ SF₅ H H n-C₅H₁₁ SF₅ H H n-C₆H₁₃ SF₅ H H H SF₅ F H CH₃ SF₅ F H C_2H5 SF₅ F H n-C₃H₇ SF₅ F H n-C₄H₉ SF₅ F H n-C₅H₁₁ SF₅ F H n-C₆H₁₃ SF₅ F H H SF₅ F F CH₃ SF₅ F F C₂H₅ SF₅ F F n-C₃H₇ SF₅ F F n-C₄H₉ SF₅ F F n-C₅H₁₁ SF₅ F F n-C₆H₁₃ SF₅ F F H CN H H CH₃ CN H H C₂H₅ CN H H n-C₃H₇ CN H H n-C₄H₉ CN H H n-C₅H₁₁ CN H H n-C₆H₁₃ CN H H H CN F H CH₃ CN F H C₂H₅ CN F H n-C₃H₇ CN F H n-C₄H₉ CN F H n-C₅H₁₁ CN F H n-C₆H₁₃ CN F H H CN F F CH₃ CN F F C₂H₅ CN F F n-C₃H₇ CN F F n-C₄H₉ CN F F n-C₅H₁₁ CN F F n-C₆H₁₃ CN F F Analogously, the following compounds of the formula

produced: R ¹ X L ¹ L ² H F H H CH ₃ F H H C ₂ H ₅ F H H nC ₄ H ₉ F H H nc ₅ H ₁₁ F H H nc ₆ H ₁₃ F H H H F F H CH ₃ F F H C ₂ H ₅ F F H nC ₃ H ₇ F F H K 41 S _B 51 N 95.9 I; Δε = 9.7; Δn = 0.0688 nC ₄ H ₉ F F H K 31 S _B 64 N 97.1 I; Δε = 9.3; Δn = 0.0621 nc ₅ H ₁₁ F F H nc ₆ H ₁₃ F F H H F F F CH ₃ F F F K 54 I, Δε = 14.8; = N = 0.0490 C ₂ H ₅ F F F K 48 N (34,7) I; △ ε = 14.1; △n = 0.054.0 nC ₃ H ₇ F F F nC ₄ H ₉ F F F K 43 N 66.1 I, △ ε = 13.3; = N = 0.0590 nc ₅ H ₁₁ F F F K 39 N 75.3 I; Δε = 11.8; = N = 0.0568 nc ₆ H ₁₃ F F F H Cl H H CH ₃ Cl H H C ₂ H ₅ Cl H H nC ₃ H ₇ Cl H H nC ₄ H ₉ Cl H H nc ₅ H ₁₁ Cl H H nc ₆ H ₁₃ Cl H H H Cl F H CH ₃ Cl F H C ₂ H ₅ Cl F H nC ₃ H ₇ Cl F H nC ₄ H ₉ Cl F H nc ₅ H ₁₁ Cl F H nc ₆ H ₁₃ Cl F H H Cl F F CH ₃ Cl F F C ₂ H ₅ Cl F F nC ₃ H ₇ Cl F F nC ₄ H ₉ Cl F F nc ₅ H ₁₁ Cl F F nc ₆ H ₁₃ Cl F F H OCF ₃ H H CH ₃ OCF ₃ H H C ₂ H ₅ OCF ₃ H H nC ₃ H ₇ OCF ₃ H H K -41 S _B 123 N 129.3 I; Δε = 9.1; Δn = 0.0780 nC ₄ H ₉ OCF ₃ H H KC -54 S _B 129 I; Δε = 9.1; An = 0.0689 nc ₅ H ₁₁ OCF ₃ H H nc ₆ H ₁₃ OCF ₃ H H H OCF ₃ F H CH ₃ OCF ₃ F H C ₂ H ₅ OCF ₃ F H nC ₃ H ₇ OCF ₃ F H S _B 74 N 105.8 I; Δε = 11.7; Δn = 0.0701 nC ₄ H ₉ OCF ₃ F H S _B 81 N 105.8 I; Δε = 11.5; Δn = 0.0623 nc ₅ H ₁₁ OCF ₃ F H nc ₆ H ₁₃ OCF ₃ F H H OCF ₃ F F CH ₃ OCF ₃ F F C ₂ H ₅ OCF ₃ F F nC ₃ H ₇ OCF ₃ F F nC ₄ H ₉ OCF ₃ F F nc ₅ H ₁₁ OCF ₃ F F nc ₆ H ₁₃ OCF ₃ F F H OCHF ₂ H H CH ₃ OCHF ₂ H H C ₂ H ₅ OCHF ₂ H H nC ₃ H ₇ OCHF ₂ H H nC ₄ H ₉ OCHF ₂ H H nc ₅ H ₁₁ OCHF ₂ H H nc ₆ H ₁₃ OCHF ₂ H H H OCHF ₂ F H CH ₃ OCHF ₂ F H C ₂ H ₅ OCHF ₂ F H nC ₃ H ₇ OCHF ₂ F H nC ₄ H ₉ OCHF ₂ F H nc ₅ H ₁₁ OCHF ₂ F H nc ₆ H ₁₃ OCHF ₂ F H H OCHF ₂ F F CH ₃ OCHF ₂ F F C ₂ H ₅ OCHF ₂ F F nC ₃ H ₇ OCHF ₂ F F nC ₄ H ₉ OCHF ₂ F F nc ₅ H ₁₁ OCHF ₂ F F nc ₆ H ₁₃ OCHF ₂ F F H OCHFCF ₃ H H CH ₃ OCHFCF ₃ H H C ₂ H ₅ OCHFCF ₃ H H nC ₃ H ₇ OCHFCF ₃ H H nC ₄ H ₉ OCHFCF ₃ H H nc ₅ H ₁₁ OCHFCF ₃ H H nc ₅ H ₁₃ OCHFCF ₃ H H H OCHFCF ₃ F H CH ₃ OCHFCF ₃ F H C ₂ H ₅ OCHFCF ₃ F H nC ₃ H ₇ OCHFCF ₃ F H nC ₄ H ₉ OCHFCF ₃ F H nc ₅ H ₁₁ OCHFCF ₃ F H nc ₆ H ₁₃ OCHFCF ₃ F H H OCHFCF3 F F CH ₃ OCHFCF ₃ F F C ₂ H ₅ OCHFCF ₃ F F nC ₃ H ₇ OCHFCF ₃ F F nC ₄ H ₉ OCHFCF ₃ F F nc ₅ H ₁₁ OCHFCF ₃ F F nc ₆ H ₁₃ OCHFCF ₃ F F H OCHFCF ₃ H H CH ₃ OCHFCF ₃ H H C ₂ H ₅ OCHFCF ₃ H H nC ₃ H ₇ OCHFCF ₃ H H nC ₄ H ₉ OCHFCF ₃ H H nc ₅ H ₁₁ OCHFCF ₃ H H nc ₆ H ₁₃ OCHFCF ₃ H H H OCHFCF ₃ F H CH ₃ OCHFCF ₃ F H C ₂ H ₅ OCHFCF ₃ F H nC ₃ H ₇ OCHFCF ₃ F H nC ₄ H ₉ OCHFCF ₃ F H nc ₅ H ₁₁ OCHFCF ₃ F H nc ₆ H ₁₃ OCHFCF ₃ F H H OCHFCF ₃ F F CH ₃ OCHFCF ₃ F F C ₂ H ₅ OCHFCF ₃ F F nC ₃ H ₇ OCHFCF ₃ F F nC ₄ H ₉ OCHFCF ₃ F F nc ₅ H ₁₁ OCHFCF ₃ F F nc ₆ H ₁₃ OCHFCF ₃ F F H OCF ₂ CHFCF ₃ H H CH ₃ OCF ₂ CHFCF ₃ H H C ₂ H ₅ OCF ₂ CHFCF ₃ H H nC ₃ H ₇ OCF ₂ CHFCF ₃ H H nC ₄ H ₉ OCF ₂ CHFCF ₃ H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H H OCF ₂ CHFCF ₃ F H CH ₃ OCF ₂ CHFCF ₃ F H C ₂ H ₅ OCF ₂ CHFCF ₃ F H nC ₃ H ₇ OCF ₂ CHFCF ₃ F H nC ₄ H ₉ OCF ₂ CHFCF3 F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H H OCF ₂ CHFCF ₃ F F CH ₃ OCF ₂ CHFCF ₃ F F C ₂ H ₅ OCF ₂ CHFCF ₃ F F nC ₃ H ₇ OCF ₂ CHFCF ₃ F F nC ₄ H ₉ OCF ₂ CHFCF ₃ F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F H NCS H H CH ₃ NCS H H C ₂ H ₅ NCS H H nC ₃ H ₇ NCS H H nC ₄ H ₉ NCS H H nc ₅ H ₁₁ NCS H H nc ₆ H ₁₃ NCS H H H NCS F H CH ₃ NCS F H C ₂ H ₅ NCS F H nC ₃ H ₇ NCS F H nC ₄ H ₉ NCS F H nc ₅ H ₁₁ NCS F H nc ₆ H ₁₃ NCS F H H NCS F F CH ₃ NCS F F C ₂ H ₅ NCS F F nC ₃ H ₇ NCS F F nC ₄ H ₉ NCS F F nc ₅ H ₁₁ NCS F F nc ₆ H ₁₃ NCS F F H C ₂ F ₅ H H CH ₃ C ₂ F ₅ H H C ₂ H ₅ C ₂ F ₅ H H nC ₃ H ₇ C ₂ F ₅ H H nC ₄ H ₉ C ₂ F ₅ H H nc ₅ H ₁₁ C ₂ F ₅ H H nc ₆ H ₁₃ C ₂ F ₅ H H H C ₂ F ₅ F H CH ₃ C ₂ F ₅ F H C ₂ H ₅ C ₂ F ₅ F H nC ₃ H ₇ C ₂ F ₅ F H nC ₄ H ₉ C ₂ F ₅ F H nc ₅ H ₁₁ C ₂ F ₅ F H nc ₆ H ₁₃ C ₂ F ₅ F H H C ₂ F ₅ F F CH ₃ C ₂ F ₅ F F C ₂ H ₅ C ₂ F ₅ F F nC ₃ H ₇ C ₂ F ₅ F F nC ₄ H ₉ C ₂ F ₅ F F nc ₅ H ₁₁ C ₂ F ₅ F F nc ₆ H ₁₃ C ₂ F ₅ F F H C ₃ F ₇ H H CH ₃ C ₃ F ₇ H H C ₂ H ₅ C ₃ F ₇ H H nC ₃ H ₇ C ₃ F ₇ H H nC ₄ H ₉ C ₃ F ₇ H H nc ₅ H ₁₁ C ₃ F ₇ H H nc ₆ H ₁₃ C ₃ F ₇ H H H C ₃ F ₇ F H CH ₃ C ₃ F ₇ F H C ₂ H ₅ C ₃ F ₇ F H nC ₃ H ₇ C ₃ F ₇ F H nC ₄ H ₉ C ₃ F ₇ F H nc ₅ H ₁₁ C ₃ F ₇ F H nc ₆ H ₁₃ C ₃ F ₇ F H H C ₃ F ₇ F F CH ₃ C ₃ F ₇ F F C ₂ H ₅ C ₃ F ₇ F F nC ₃ H ₇ C ₃ F ₇ F F nC ₄ H ₉ C ₃ F ₇ F F nc ₅ H ₁₁ C ₃ F ₇ F F nc ₆ H ₁₃ C ₃ F ₇ F F H SF ₅ H H CH ₃ SF ₅ H H C ₂ H ₅ SF ₅ H H nC ₃ H ₇ SF ₅ H H nC ₄ H ₉ SF ₅ H H nc ₅ H ₁₁ SF ₅ H H nc ₆ H ₁₃ SF ₅ H H H SF ₅ F H CH ₃ SF ₅ F H C _2H5 SF ₅ F H nC ₃ H ₇ SF ₅ F H nC ₄ H ₉ SF ₅ F H nc ₅ H ₁₁ SF ₅ F H nc ₆ H ₁₃ SF ₅ F H H SF ₅ F F CH ₃ SF ₅ F F C ₂ H ₅ SF ₅ F F nC ₃ H ₇ SF ₅ F F nC ₄ H ₉ SF ₅ F F nc ₅ H ₁₁ SF ₅ F F nc ₆ H ₁₃ SF ₅ F F H CN H H CH ₃ CN H H C ₂ H ₅ CN H H nC ₃ H ₇ CN H H nC ₄ H ₉ CN H H nc ₅ H ₁₁ CN H H nc ₆ H ₁₃ CN H H H CN F H CH ₃ CN F H C ₂ H ₅ CN F H nC ₃ H ₇ CN F H nC ₄ H ₉ CN F H nc ₅ H ₁₁ CN F H nc ₆ H ₁₃ CN F H H CN F F CH ₃ CN F F C ₂ H ₅ CN F F nC ₃ H ₇ CN F F nC ₄ H ₉ CN F F nc ₅ H ₁₁ CN F F nc ₆ H ₁₃ CN F F

Example 2 Step 2.1

A mixture of 50 mmol of I , 50 mmol of J , 2.5 mmol of Pd (PPh ₃ ) ₄ , 300 ml of toluene and 300 ml of Na borate buffer (pH = 9) is stirred at 80 ° C. for 18 h. The mixture is poured into 500 ml of 0.1 N HCl, the product is extracted with CH ₂ Cl ₂ , dried over Na ₂ SO ₄ and rotated to dryness. The crude product is in chromatographed on Kiegelgel n-heptane and then recrystallized twice at -20 ° C from n-heptane. K 78 N 93.1 I; Δn = 0.1493; Δε = 27.3

hergestellt: R¹ X L¹ L² L³ L⁴ H F H H H H CH₃ F H H H H C₂H₅ F H H H H C₃H₇ F H H H H n-C₄H₉ F H H H H n-C₅H₁₁ F H H H H n-C₆H₁₃ F H H H H H F F H H H CH₃ F F H H H C₂H₅ F F H H H n-C₃H₇ F F H H H n-C₄H₉ F F H H H n-C₅H₁₁ F F H H H n-C₆H₁₃ F F H H H H F F F H H CH₃ F F F H H n-C₃H₇ F F F H H K 75 N 118,0 I; Δε = 23,2; Δn = 0,1450 n-C₄H₉ F F F H H n-C₅H₁₁ F F F H H n-C₆H₁₃ F F F H H H Cl H H H H CH₃ Cl H H H H C₂H₅ Cl H H H H n-C₃H₇ Cl H H H H n-C₄H₉ Cl H H H H n-C₅H₁₁ Cl H H H H n-C₆H₁₃ Cl H H H H H Cl F H H H CH₃ Cl F H H H C₂H₅ Cl F H H H n-C₃H₇ Cl F H H H n-C₄H₉ Cl F H H H n-C₅H₁₁ Cl F H H H n-C₆H₁₃ Cl F H H H H Cl F F H H CH₃ Cl F F H H C₂H₅ Cl F F H H n-C₃H₇ Cl F F H H n-C₄H₉ Cl F F H H n-C₅H₁₁ Cl F F H H n-C₆H₁₃ Cl F F H H H OCF₃ H H H H CH₃ OCF₃ H H H H C₂H₅ OCF₃ H H H H n-C₃H₇ OCF₃ H H H H n-C₄H₉ OCF₃ H H H H n-C₅H₁₁ OCF₃ H H H H n-C₆H₁₃ OCF₃ H H H H H OCF₃ F H H H CH₃ OCF₃ F H H H C₂H₅ OCF₃ F H H H n-C₃H₇ OCF₃ F H H H n-C₄H₉ OCF₃ F H H H n-C₅H₁₁ OCF₃ F H H H n-C₆H₁₃ OCF₃ F H H H H OCF₃ F F H H CH₃ OCF₃ F F H H C₂H₅ OCF₃ F F H H n-C₃H₇ OCF₃ F F H H n-C₄H₉ OCF₃ F F H H n-C₅H₁₁ OCF₃ F F H H n-C₆H₁₃ OCF₃ F F H H H OCHF₂ H H H H CH₃ OCHF₂ H H H H C₂H₅ OCHF₂ H H H H n-C₃H₇ OCHF₂ H H H H n-C₄H₉ OCHF₂ H H H H n-C₅H₁₁ OCHF₂ H H H H n-C₆H₁₃ OCHF₂ H H H H H OCHF₂ F H H H CH₃ OCHF₂ F H H H C₂H₅ OCHF₂ F H H H n-C₃H₇ OCHF₂ F H H H n-C₄H₉ OCHF₂ F H H H n-C₅H₁₁ OCHF₂ F H H H n-C₆H₁₃ OCHF₂ F H H H H OCHF₂ F F H H CH₃ OCHF₂ F F H H C₂H₅ OCHF₂ F F H H n-C₃H₇ OCHF₂ F F H H n-C₄H₉ OCHF₂ F F H H n-C₅H₁₁ OCHF₂ F F H H n-C₆H₁₃ OCHF₂ F F H H H OCHFCF₃ H H H H CH₃ OCHFCF₃ H H H H C₂H₅ OCHFCF₃ H H H H n-C₃H₇ OCHFCF₃ H H H H n-C₄H₉ OCHFCF₃ H H H H n-C₅H₁₁ OCHFCF₃ H H H H n-C₆H₁₃ OCHFCF₃ H H H H H OCHFCF₃ F H H H CH₃ OCHFCF₃ F H H H C₂H₅ OCHFCF₃ F H H H n-C₃H₇ OCHFCF₃ F H H H n-C₄H₉ OCHFCF₃ F H H H n-C₅H₁₁ OCHFCF₃ F H H H n-C₆H₁₃ OCHFCF₃ F H H H H OCHFCF₃ F F H H CH₃ OCHFCF₃ F F H H C₂H₅ OCHFCF₃ F F H H n-C₃H₇ OCHFCF₃ F F H H n-C₄H₉ OCHFCF₃ F F H H n-C₅H₁₁ OCHFCF₃ F F H H n-C₆H₁₃ OCHFCF₃ F F H H H OCHFCF₃ H H H H CH₃ OCHFCF₃ H H H H C₂H₅ OCHFCF₃ H H H H n-C₃H₇ OCHFCF₃ H H H H n-C₄H₉ OCHFCF₃ H H H H n-C₅H₁₁ OCHFCF₃ H H H H n-C₆H₁₃ OCHFCF₃ H H H H H OCHFCF₃ F H H H CH₃ OCHFCF₃ F H H H C₂H₅ OCHFCF₃ F H H H n-C₃H₇ OCHFCF₃ F H H H n-C₄H₉ OCHFCF₃ F H H H n-C₅H₁₁ OCHFCF₃ F H H H n-C₆H₁₃ OCHFCF₃ F H H H H OCHFCF₃ F F H H CH₃ OCHFCF₃ F F H H C₂H₅ OCHFCF₃ F F H H n-C₃H₇ OCHFCF₃ F F H H n-C₄H₉ OCHFCF₃ F F H H n-C₅H₁₁ OCHFCF₃ F F H H n-C₆H₁₃ OCHFCF₃ F F H H H OCF₂CHFCF₃ H H H H CH₃ OCF₂CHFCF₃ H H H H C₂H₅ OCF₂CHFCF₃ H H H H n-C₃H₇ OCF₂CHFCF₃ H H H H n-C₄H₉ OCF₂CHFCF₃ H H H H n-C₅H₁₁ OCF₂CHFCF₃ H H H H n-C₆H₁₃ OCF₂CHFCF₃ H H H H H OCF₂CHFCF₃ F H H H CH₃ OCF₂CHFCF₃ F H H H C₂H₅ OCF₂CHFCF₃ F H H H n-C₃H₇ OCF₂CHFCF₃ F H H H n-C₄H₉ OCF₂CHFCF₃ F H H H n-C₅H₁₁ OCF₂CHFCF₃ F H H H n-C₆H₁₃ OCF₂CHFCF₃ F H H H H OCF₂CHFCF₃ F F H H CH₃ OCF₂CHFCF₃ F F H H C₂H₅ OCF₂CHFCF₃ F F H H n-C₃H₇ OCF₂CHFCF₃ F F H H n-C₄H₉ OCF₂CHFCF₃ F F H H n-C₅H₁₁ OCF₂CHFCF₃ F F H H n-C₆H₁₃ OCF₂CHFCF₃ F F H H H NCS H H H H CH₃ NCS H H H H C₂H₅ NCS H H H H n-C₃H₇ NCS H H H H n-C₄H₉ NCS H H H H n-C₅H₁₁ NCS H H H H n-C₆H₁₃ NCS H H H H H NCS F H H H CH₃ NCS F H H H C₂H₅ NCS F H H H n-C₃H₇ NCS F H H H n-C₄H₉ NCS F H H H n-C₅H₁₁ NCS F H H H n-C₆H₁₃ NCS F H H H H NCS F F H H CH₃ NCS F F H H C₂H₅ NCS F F H H n-C₃H₇ NCS F F H H n-C₄H₉ NCS F F H H n-C₅H₁₁ NCS F F H H n-C₆H₁₃ NCS F F H H H C₂F₅ H H H H CH₃ C₂F₅ H H H H C₂H₅ C₂F₅ H H H H n-C₃H₇ C₂F₅ H H H H n-C₄H₉ C₂F₅ H H H H n-C₅H₁₁ C₂F₅ H H H H n-C₆H₁₃ C₂F₅ H H H H H C₂F₅ F H H H CH₃ C₂F₅ F H H H C₂H₅ C₂F₅ F H H H n-C₃H₇ C₂F₅ F H H H n-C₄H₉ C₂F₅ F H H H n-C₅H₁₁ C₂F₅ F H H H n-C₆H₁₃ C₂F₅ F H H H H C₂F₅ F F H H CH₃ C₂F₅ F F H H C₂H₅ C₂F₅ F F H H n-C₃H₇ C₂F₅ F F H H n-C₄H₉ C₂F₅ F F H H n-C₅H₁₁ C₂F₅ F F H H n-C₆H₁₃ C₂F₅ F F H H H C₃F₇ H H H H CH₃ C₃F₇ H H H H C₂H₅ C₃F₇ H H H H n-C₃H₇ C₃F₇ H H H H n-C₄H₉ C₃F₇ H H H H n-C₅H₁₁ C₃F₇ H H H H n-C₆H₁₃ C₃F₇ H H H H H C₃F₇ F H H H CH₃ C₃F₇ F H H H C₂H₅ C₃F₇ F H H H n-C₃H₇ C₃F₇ F H H H n-C₄H₉ C₃F₇ F H H H n-C₅H₁₁ C₃F₇ F H H H n-C₆H₁₃ C₃F₇ F H H H H C₃F₇ F F H H CH₃ C₃F₇ F F H H C₂H₅ C₃F₇ F F H H n-C₃H₇ C₃F₇ F F H H n-C₄H₉ C₃F₇ F F H H n-C₅H₁₁ C₃F₇ F F H H n-C₆H₁₃ C₃F₇ F F H H H SF₅ H H H H CH₃ SF₅ H H H H C₂H₅ SF₅ H H H H n-C₃H₇ SF₅ H H H H n-C₄H₉ SF₅ H H H H n-C₅H₁₁ SF₅ H H H H n-C₆H₁₃ SF₅ H H H H H SF₅ F H H H CH₃ SF₅ F H H H C₂H₅ SF₅ F H H H n-C₃H₇ SF₅ F H H H n-C₄H₉ SF₅ F H H H n-C₅H₁₁ SF₅ F H H H n-C₆H₁₃ SF₅ F H H H H SF₅ F F H H CH₃ SF₅ F F H H C₂H₅ SF₅ F F H H n-C₃H₇ SF₅ F F H H n-C₄H₉ SF₅ F F H H n-C₅H₁₁ SF₅ F F H H n-C₆H₁₃ SF₅ F F H H H CN H H H H CH₃ CN H H H H C₂H₅ CN H H H H n-C₃H₇ CN H H H H n-C₄H₉ CN H H H H n-C₅H₁₁ CN H H H H n-C₆H₁₃ CN H H H H H CN F H H H CH₃ CN F H H H C₂H₅ CN F H H H n-C₃H₇ CN F H H H n-C₄H₉ CN F H H H n-C₅H₁₁ CN F H H H n-C₆H₁₃ CN F H H H H CN F F H H CH₃ CN F F H H C₂H₅ CN F F H H n-C₃H₇ CN F F H H n-C₄H₉ CN F F H H n-C₅H₁₁ CN F F H H n-C₆H₁₃ CN F F H H H F H H F H CH₃ F H H F H C₂H₅ F H H F H C₃H₇ F H H F H n-C₄H₉ F H H F H n-C₅H₁₁ F H H F H n-C₆H₁₃ F H H F H H F F H F H CH₃ F F H F H C₂H₅ F F H F H n-C₃H₇ F F H F H n-C₄H₉ F F H F H n-C₅H₁₁ F F H F H n-C₆H₁₃ F F H F H H F F F F H CH₃ F F F F H C₂H₅ F F F F H K 89 N (76,8) I, Δε = 29,9; Δn = 0,1310 n-C₃H₇ F F F F H K 70 N 102,3 I; Δε = 29,7; Δn = 0,1364 n-C₄H₉ F F F F H n-C₅H₁₁ F F F F H n-C₆H₁₃ F F F F H H Cl H H F H CH₃ Cl H H F H C₂H₅ Cl H H F H n-C₃H₇ Cl H H F H n-C₄H₉ Cl H H F H n-C₅H₁₁ Cl H H F H n-C₆H₁₃ Cl H H F H H Cl F H F H CH₃ Cl F H F H C₂H₅ Cl F H F H n-C₃H₇ Cl F H F H n-C₄H₉ Cl F H F H n-C₅H₁₁ Cl F H F H n-C₆H₁₃ Cl F H F H H Cl F F F H CH₃ Cl F F F H C₂H₅ Cl F F F H n-C₃H₇ Cl F F F H n-C₄H₉ Cl F F F H n-C₅H₁₁ Cl F F F H n-C₆H₁₃ Cl F F F H H OCF₃ H H F H CH₃ OCF₃ H H F H C₂H₅ OCF₃ H H F H n-C₃H₇ OCF₃ H H F H n-C₄H₉ OCF₃ H H F H n-C₅H₁₁ OCF₃ H H F H n-C₆H₁₃ OCF₃ H H F H H OCF₃ F H F H CH₃ OCF₃ F H F H C₂H₅ OCF₃ F H F H n-C₃H₇ OCF₃ F H F H n-C₄H₉ OCF₃ F H F H n-C₅H11 OCF₃ F H F H n-C₆H₁₃ OCF₃ F H F H H OCF₃ F F F H CH₃ OCF₃ F F F H C₂H₅ OCF₃ F F F H n-C₃H₇ OCF₃ F F F H n-C₄H_s OCF₃ F F F H n-C₅H₁₁ OCF₃ F F F H n-C₆H₁₃ OCF₃ F F F H H OCHF₂ H H F H CH₃ OCHF₂ H H F H C₂H₅ OCHF₂ H H F H n-C₃H₇ OCHF₂ H H F H n-C₄H₉ OCHF₂ H H F H n-C₅H₁₁ OCHF₂ H H F H n-C₆H₁₃ OCHF₂ H H F H H OCHF₂ F H F H CH₃ OCHF₂ F H F H C₂H₅ OCHF₂ F H F H n-C₃H₇ OCHF₂ F H F H n-C₄H₉ OCHF₂ F H F H n-C₅H₁₁ OCHF₂ F H F H n-C₆H₁₃ OCHF₂ F H F H H OCHF₂ F F F H CH₃ OCHF₂ F F F H C₂H₅ OCHF₂ F F F H n-C₃H₇ OCHF₂ F F F H n-C₄H₉ OCHF₂ F F F H n-C₅H₁₁ OCHF₂ F F F H n-C₆H₁₃ OCHF₂ F F F H H OCHFCF₃ H H F H CH₃ OCHFCF₃ H H F H C₂H₅ OCHFCF₃ H H F H n-C₃H₇ OCHFCF₃ H H F H n-C₄H₉ OCHFCF₃ H H F H n-C₅H₁₁ OCHFCF₃ H H F H n-C₆H₁₃ OCHFCF₃ H H F H H OCHFCF₃ F H F H CH₃ OCHFCF₃ F H F H C₂H₅ OCHFCF₃ F H F H n-C₃H₇ OCHFCF₃ F H F H n-C₄H₉ OCHFCF₃ F H F H n-C₅H₁₁ OCHFCF₃ F H F H n-C₆H₁₃ OCHFCF₃ F H F H H OCHFCF₃ F F F H CH₃ OCHFCF₃ F F F H C₂H₅ OCHFCF₃ F F F H n-C₃H₇ OCHFCF₃ F F F H n-C₄H₉ OCHFCF₃ F F F H n-C₅H₁₁ OCHFCF₃ F F F H n-C₆H₁₃ OCHFCF₃ F F F H H OCHFCF₃ H H F H CH₃ OCHFCF₃ H H F H C₂H₅ OCHFCF₃ H H F H n-C₃H₇ OCHFCF₃ H H F H n-C₄H₉ OCHFCF₃ H H F H n-C₅H₁₁ OCHFCF₃ H H F H n-C₆H₁₃ OCHFCF₃ H H F H H OCHFCF₃ F H F H CH₃ OCHFCF₃ F H F H C₂H₅ OCHFCF₃ F H F H n-C₃H₇ OCHFCF₃ F H F H n-C₄H₉ OCHFCF₃ F H F H n-C₅H₁₁ OCHFCF₃ F H F H n-C₆H₁₃ OCHFCF₃ F H F H H OCHFCF₃ F F F H CH₃ OCHFCF₃ F F F H C₂H₅ OCHFCF₃ F F F H n-C₃H₇ OCHFCF₃ F F F H n-C₄H₉ OCHFCF₃ F F F H n-C₅H₁₁ OCHFCF₃ F F F H n-C₆H₁₃ OCHFCF₃ F F F H H OCF₂CHFCF₃ H H F H CH₃ OCF₂CHFCF₃ H H F H C₂H₅ OCF₂CHFCF₃ H H F H n-C₃H₇ OCF₂CHFCF₃ H H F H n-C₄H₉ OCF₂CHFCF₃ H H F H n-C₅H₁₁ OCF₂CHFCF₃ H H F H n-C₆H₁₃ OCF₂CHFCF₃ H H F H H OCF₂CHFCF₃ F H F H CH₃ OCF₂CHFCF₃ F H F H C₂H₅ OCF₂CHFCF₃ F H F H n-C₃H₇ OCF₂CHFCF₃ F H F H n-C₄H₉ OCF₂CHFCF₃ F H F H n-C₅H₁₁ OCF₂CHFCF₃ F H F H n-C₆H₁₃ OCF₂CHFCF₃ F H F H H OCF₂CHFCF₃ F F F H CH₃ OCF₂CHFCF₃ F F F H C₂H₅ OCF₂CHFCF₃ F F F H n-C₃H₇ OCF₂CHFCF₃ F F F H n-C₄H₉ OCF₂CHFCF₃ F F F H n-C₅H₁₁ OCF₂CHFCF₃ F F F H n-C₆H₁₃ OCF₂CHFCF₃ F F F H H NCS H H F H CH₃ NCS H H F H C₂H₅ NCS H H F H n-C₃H₇ NCS H H F H n-C₄H₉ NCS H H F H n-C₅H₁₁ NCS H H F H n-C₆H₁₃ NCS H H F H H NCS F H F H CH₃ NCS F H F H C₂H₅ NCS F H F H n-C₃H₇ NCS F H F H n-C₄H₉ NCS F H F H n-C₅H₁₁ NCS F H F H n-C₆H₁₃ NCS F H F H H NCS F F F H CH₃ NCS F F F H C₂H₅ NCS F F F H n-C₃H₇ NCS F F F H n-C₄H₉ NCS F F F H n-C₅H₁₁ NCS F F F H n-C₆H₁₃ NCS F F F H H C₂F₅ H H F H CH₃ C₂F₅ H H F H C₂H₅ C₂F₅ H H F H n-C₃H₇ C₂F₅ H H F H n-C₄H₉ C₂F₅ H H F H n-C₅H₁₁ C₂F₅ H H F H n-C₆H₁₃ C₂F₅ H H F H H C₂F₅ F H F H CH₃ C₂F₅ F H F H C₂H₅ C₂F₅ F H F H n-C₃H₇ C₂F₅ F H F H n-C₄H₉ C₂F₅ F H F H n-C₅H₁₁ C₂F₅ F H F H n-C₆H₁₃ C₂F₅ F H F H H C₂F₅ F F F H CH₃ C₂F₅ F F F H C₂H₅ C₂F₅ F F F H n-C₃H₇ C₂F₅ F F F H n-C4H9 C₂F₅ F F F H n-C₅H₁₁ C₂F₅ F F F H n-C₆H₁₃ C₂F₅ F F F H H C₃F₇ H H F H CH₃ C₃F₇ H H F H C₂H₅ C₃F₇ H H F H n-C₃H₇ C₃F₇ H H F H n-C₄H₉ C₃F₇ H H F H n-C₅H₁₁ C₃F₇ H H F H n-C₆H₁₃ C₃F₇ H H F H H C₃F₇ F H F H CH₃ C₃F₇ F H F H C₂H₅ C₃F₇ F H F H n-C₃H₇ C₃F₇ F H F H n-C₄H₉ C₃F₇ F H F H n-C₅H₁₁ C₃F₇ F H F H n-C₆H₁₃ C₃F₇ F H F H H C₃F₇ F F F H CH₃ C₃F₇ F F F H C₂H₅ C₃F₇ F F F H n-C₃H₇ C₃F₇ F F F H n-C₄H₉ C₃F₇ F F F H n-C₅H₁₁ C₃F₇ F F F H n-C₆H₁₃ C₃H₇ F F F H H SF₅ H H F H CH₃ SF₅ H H F H C₂H₅ SF₅ H H F H n-C₃H₇ SF₅ H H F H n-C₄H₉ SF₅ H H F H n-C₅H₁₁ SF₅ H H F H n-C₆H₁₃ SF₅ H H F H H SF₅ F H F H CH₃ SF₅ F H F H C₂H₅ SF₅ F H F H n-C₃H₇ SF₅ F H F H n-C₄H₉ SF₅ F H F H n-C₅H₁₁ SF₅ F H F H n-C₆H₁₃ SF₅ F H F H H SF₅ F F F H CH₃ SF₅ F F F H C₂H₅ SF₅ F F F H n-C₃H₇ SF₅ F F F H n-C₄H₉ SF₅ F F F H n-C₅H₁₁ SF₅ F F F H n-C₆H₁₃ SF₅ F F F H H CN H H F H CH₃ CN H H F H C₂H₅ CN H H F H n-C₃H₇ CN H H F H n-C₄H₉ CN H H F H n-C₅H₁₁ CN H H F H n-C₆H₁₃ CN H H F H H CN F H F H CH₃ CN F H F H C₂H₅ CN F H F H n-C₃H₇ CN F H F H n-C₄H₉ CN F H F H n-C₅H₁₁ CN F H F H n-C₆H₁₃ CN F H F H H CN F F F H CH₃ CN F F F H C₂H₅ CN F F F H n-C₃H₇ CN F F F H n-C₄H₉ CN F F F H n-C₅H₁₁ CN F F F H n-C₆H₁₃ CN F F F H H F H H F F CH₃ F H H F F C₂H₅ F H H F F n-C₄H₉ F H H F F n-C₅H₁₁ F H H F F n-C₆H₁₃ F H H F F H F F F H F F CH₃ F F H F F C₂H₅ F F H F F n-C₃H₇ F F H F F n-C₄H₉ F F H F F n-C₅H₁₁ F F H F F n-C₆H₁₃ F F H F F H F F F F F CH₃ F F F F F C₂H₅ F F F F F C₂H₅ F F F F F K 91 N (58,8) I; Δε = 35, 0; Δn = 0,1149 n-C₃H₇ F F F F F K 83 N (83,0) I; Δε = 34,9; Δn = 0,1231 n-C₄H₉ F F F F F K 90 N 79,4 I; Δε = 32,4; Δn = 0,1171 n-C₅H₁₁ F F F F F K 82 N 84,3 I; Δε = 31,9; Δn = 0,1205 n-C₆H₁₃ F F F F F K 89 N (83,4) I; Δε = 30,6; Δn = 0,1116 n-C₇H₁₅ F F F F F K 82 N 84,3 I; Δε =30,3; Δn = 0,1130 H Cl H H F F CH₃ Cl H H F F C₂H₅ Cl H H F F n-C₃H₇ Cl H H F F n-C₄H₉ Cl H H F F n-C₅H₁₁ Cl H H F F n-C₆H₁₃ Cl H H F F H Cl F H F F CH₃ Cl F H F F C₂H₅ Cl F H F F n-C₃H₇ Cl F H F F n-C₄H₉ Cl F H F F n-C₅H₁₁ Cl F H F F n-C₆H₁₃ Cl F H F F H Cl F F F F CH₃ Cl F F F F C₂H₅ Cl F F F F n-C₃H₇ Cl F F F F K 80 N 106,7 I; Δε = 31,5; Δn = 0,1372 n-C₄H₉ Cl F F F F n-C₅H₁₁ Cl F F F F n-C₆H₁₃ Cl F F F F H OCF₃ H H F F CH₃ OCF₃ H H F F C₂H₅ OCF₃ H H F F n-C₃H₇ OCF₃ H H F F K 80 N 119,8 I; Δε = 25,3; Δn = 0,1330 n-C₄H₉ OCF₃ H H F F n-C₅H₁₁ OCF₃ H H F F n-C₆H₁₃ OCF₃ H H F F H OCF₃ F H F F CH₃ OCF₃ F H F F C₂H₅ OCF₃ F H F F n-C₃H₇ OCF₃ F H F F K 48 S_A (46) N 105,1 I; Δε = 29,8; An = 0,1180 n-C₄H₉ OCF₃ F H F F n-C₅H₁₁ OCF₃ F H F F n-C₆H₁₃ OCF₃ F H F F H OCF₃ F F F F CH₃ OCF₃ F F F F C₂H₅ OCF₃ F F F F n-C₃H₇ OCF₃ F F F F K 73 N 97,5 I; Δε = 35,6; Δn = 0,1158 n-C₄H₉ OCF₃ F F F F n-C₅H₁₁ OCF₃ F F F F n-C₆H₁₃ OCF₃ F F F F H OCHF₂ H H F F CH₃ OCHF₂ H H F F C₂H₅ OCHF₂ H H F F n-C₃H₇ OCHF₂ H H F F n-C₄H₉ OCHF₂ H H F F n-C₅H₁₁ OCHF₂ H H F F n-C₆H₁₃ OCHF₂ H H F F H OCHF₂ F H F F CH₃ OCHF₂ F H F F C₂H₅ OCHF₂ F H F F n-C₃H₇ OCHF₂ F H F F n-C₄H₉ OCHF₂ F H F F n-C₅H₁₁ OCHF₂ F H F F n-C₆H₁₃ OCHF₂ F H F F H OCHF₂ F F F F CH₃ OCHF₂ F F F F C₂H₅ OCHF₂ F F F F n-C₃H₇ OCHF₂ F F F F n-C₄H₉ OCHF₂ F F F F n-C₅H₁₁ OCHF₂ F F F F n-C₆H₁₃ OCHF₂ F F F F H OCHFCF₃ H H F F CH₃ OCHFCF₃ H H F F C₂H₅ OCHFCF₃ H H F F n-C₃H₇ OCHFCF₃ H H F F n-C₄H₉ OCHFCF₃ H H F F n-C₅H₁₁ OCHFCF₃ H H F F n-C₆H₁₃ OCHFCF₃ H H F F H OCHFCF₃ F H F F CH₃ OCHFCF₃ F H F F C₂H₅ OCHFCF₃ F H F F n-C₃H₇ OCHFCF₃ F H F F n-C₄H₉ OCHFCF₃ F H F F n-C₅H₁₁ OCHFCF₃ F H F F n-C₆H₁₃ OCHFCF₃ F H F F H OCHFCF₃ F F F F CH₃ OCHFCF₃ F F F F C₂H₅ OCHFCF₃ F F F F n-C₃H₇ OCHFCF₃ F F F F n-C₄H₉ OCHFCF₃ F F F F n-C₅H₁₁ OCHFCF₃ F F F F n-C₆H₁₃ OCHFCF₃ F F F F H OCHFCF₃ H H F F CH₃ OCHFCF₃ H H F F C₂H₅ OCHFCF₃ H H F F n-C₃H₇ OCHFCF₃ H H F F n-C₄H₉ OCHFCF₃ H H F F n-C₅H₁₁ OCHFCF₃ H H F F n-C₆H₁₃ OCHFCF₃ H H F F H OCHFCF₃ F H F F CH₃ OCHFCF₃ F H F F C₂H₅ OCHFCF₃ F H F F n-C₃H₇ OCHFCF₃ F H F F n-C₄H₉ OCHFCF₃ F H F F n-C₅H₁₁ OCHFCF₃ F H F F n-C₆H₁₃ OCHFCF₃ F H F F H OCHFCF₃ F F F F CH₃ OCHFCF₃ F F F F C₂H₅ OCHFCF₃ F F F F n-C₃H₇ OCHFCF₃ F F F F n-C₄H₉ OCHFCF₃ F F F F n-C₅H₁₁ OCHFCF₃ F F F F n-C₆H₁₃ OCHFCF₃ F F F F H OCF₂CHFCF₃ . H H F F CH₃ OCF₂CHFCF₃ H H F F C₂H₅ OCF₂CHFCF₃ H H F F n-C₃H₇ OCF₂CHFCF₃ H H F F n-C₄H₉ OCF₂CHFCF₃ H H F F n-C₅H₁₁ OCF₂CHFCF₃ H H F F n-C₆H₁₃ OCF₂CHFCF₃ H H F F H OCF₂CHFCF₃ F H F F CH₃ OCF₂CHFCF₃ F H F F C₂H₅ OCF₂CHFCF₃ F H F F n-C₃H₇ OCF₂CHFCF₃ F H F F n-C₄H₉ OCF₂CHFCF₃ F H F F n-C₅H₁₁ OCF₂CHFCF₃ F H F F n-C₆H₁₃ OCF₂CHFCF₃ F H F F H OCF₂CHFCF₃ F F F F CH₃ OCF₂CHFCF₃ F F F F C₂H₅ OCF₂CHFCF₃ F F F F n-C₃H₇ OCF₂CHFCF₃ F F F F n-C₄H₉ OCF₂CHFCF₃ F F F F n-C₅H₁₁ OCF₂CHFCF₃ F F F F n-C₆H₁₃ OCF₂CHFCF₃ F F F F H NCS H H F F CH₃ NCS H H F F C₂H₅ NCS H H F F n-C₃H₇ NCS H H F F K 107 N 185,5 I; Δε = 31,4; Δn = 0,2052 n-C₄H₉ NCS H H F F n-C₅H₁₁ NCS H H F F n-C₆H₁₃ NCS H H F F H NCS F H F F CH₃ NCS F H F F C₂H₅ NCS F H F F n-C₃H₇ NCS F H F F n-C₄H₉ NCS F H F F n-C₅H₁₁ NCS F H F F n-C₆H₁₃ NCS F H F F H NCS F F F F CH₃ NCS F F F F C₂H₅ NCS F F F F n-C₃H₇ NCS F F F F n-C₄H₉ NCS F F F F n-C₅H₁₁ NCS F F F F n-C₆H₁₃ NCS F F F F H C₂F₅ H H F F CH₃ C₂F₅ H H F F C₂H₅ C₂F₅ H H F F n-C₃H₇ C₂F₅ H H F F n-C₄H₉ C₂F₅ H H F F n-C₅H₁₁ C₂F₅ H H F F n-C₆H₁₃ C₂F₅ H H F F H C₂F₅ F H F F CH₃ C₂F₅ F H F F C₂H₅ C₂F₅ F H F F n-C₃H₇ C₂F₅ F H F F n-C₄H₉ C₂F₅ F H F F n-C₅H₁₁ C₂F₅ F H F F n-C₆H₁₃ C₂F₅ F H F F H C₂F₅ F F F F CH₃ C₂F₅ F F F F C₂H₅ C₂F₅ F F F F n-C₃H₇ C₂F₅ F F F F n-C₄H₉ C₂F₅ F F F F n-C₅H₁₁ C₂F₅ F F F F n-C₆H₁₃ C₂F₅ F F F F H C₃F₇ H H F F CH₃ C₃F₇ H H F F C₂H₅ C₃F₇ H H F F n-C₃H₇ C₃F₇ H H F F n-C₄H₉ C₃F₇ H H F F n-C₅H₁₁ C₃F₇ H H F F n-C₆H₁₃ C₃F₇ H H F F H C₃F₇ F H F F CH₃ C₃F₇ F H F F C₂H₅ C₃F₇ F H F F n-C₃H₇ C₃F₇ F H F F n-C₄H₉ C₃F₇ F H F F n-C₅H₁₁ C₃F₇ F H F F n-C₆H₁₃ C₃F₇ F H F F H C₃F₇ F F F F CH₃ C₃F₇ F F F F C₂H₅ C₃F₇ F F F F n-C₃H₇ C₃F₇ F F F F n-C₄H₉ C₃F₇ F F F F n-C₅H₁₁ C₃F₇ F F F F n-C₆H₁₃ C₃F₇ F F F F H SF₅ H H F F CH₃ SF₅ H H F F C₂H₅ SF₅ H H F F n-C₃H₇ SF₅ H H F F n-C₄H₉ SF₅ H H F F n-C₅H₁₁ SF₅ H H F F n-C₆H₁₃ SF₅ H H F F H SF₅ F H F F CH₃ SF₅ F H F F C₂H₅ SF₅ F H F F n-C₃H₇ SF₅ F H F F n-C₄H₉ SF₅ F H F F n-C₅H₁₁ SF₅ F H F F n-C₆H₁₃ SF₅ F H F F H SF₅ F F F F CH₃ SF₅ F F F F C₂H₅ SF₅ F F F F n-C₃H₇ SF₅ F F F F K 110 N (83,4) I; △ε = 33,8; Δn = 0,121 I n-C₄H₉ SF₅ F F F F n-C₅H₁₁ SF₅ F F F F n-C₆H₁₃ SF₅ F F F F H CN H H F F CH₃ CN H H F F C₂H₅ CN H H F F n-C₃H₇ CN H H F F n-C₄H₉ CN H H F F n-C₅H₁₁ CN H H F F n-C₆H₁₃ CN H H F F H CN F H F F CH₃ CN F H F F C₂H₅ CN F H F F n-C₃H₇ CN F H F F n-C₄H₉ CN F H F F n-C₅H₁₁ CN F H F F n-C₆H₁₃ CN F H F F H CN F F F F CH₃ CN F F F F C₂H₅ CN F F F F K 98 N_Re (71) Sc (84) N 127,6I Δs = 67,8; △n = 0,1459 n-C₃H₇ CN F F F F K 75 S_c? (65) N 144,1 I Δn = 0,1561; As = 66,5 n-C₄H₉ CN F F F F K 79 N 139,3 I; Δε = 64,2; Δn = 0,1477 n-C₅H₁₁ CN F F F F K 65 S_c (44) N 141,5 I; Δε = 61,8; △n = 0,1490 n-C₆H₁₃ CN F F F F n-C₇H₁₅ CN F F F F K 51 N 130,8 I; Δε = 58,4; △n = 0,1459 H CF₃ H H F F C₂Hs CF₃ H H F F n-C₃H₇ CF₃ H H F F K 95 N (87,5) I; Δε = 31,5; △n = 0,1330 n-C₄H₉ CF₃ H H F F n-C₅H₁₁ CF₃ H H F F n-C₆H₁₃ CF₃ H H F F CH₂=CH CF₃ H H F F H CF₃ F F F F C₂H₅ CF₃ F F F F n-C₃H₇ CF₃ F F F F K 91 I; Δn = 0,1190; Δε = 40,8 n-C₄H₉ CF₃ F F F F n-C₅H₁₁ CF₃ F F F F n-C₆H₁₃ CF₃ F F F F CH₂=CH CF₃ F F F F H F H H F F C₂H₅ F H H F F n-C₃H₇ F H H F F n-C₄H₉ F H H F F n-C₅H₁₁ F H H F F n-C₆H₁₃ F H H F F CH₂=CH F H H F F Analogously, the following compounds of the formula

produced: R ¹ X L ¹ L ² L ³ L ⁴ H F H H H H CH ₃ F H H H H C ₂ H ₅ F H H H H C ₃ H ₇ F H H H H nC ₄ H ₉ F H H H H nc ₅ H ₁₁ F H H H H nc ₆ H ₁₃ F H H H H H F F H H H CH ₃ F F H H H C ₂ H ₅ F F H H H nC ₃ H ₇ F F H H H nC ₄ H ₉ F F H H H nc ₅ H ₁₁ F F H H H nc ₆ H ₁₃ F F H H H H F F F H H CH ₃ F F F H H nC ₃ H ₇ F F F H H K 75 N 118.0 I; Δε = 23.2; Δn = 0.1450 nC ₄ H ₉ F F F H H nc ₅ H ₁₁ F F F H H nc ₆ H ₁₃ F F F H H H Cl H H H H CH ₃ Cl H H H H C ₂ H ₅ Cl H H H H nC ₃ H ₇ Cl H H H H nC ₄ H ₉ Cl H H H H nc ₅ H ₁₁ Cl H H H H nc ₆ H ₁₃ Cl H H H H H Cl F H H H CH ₃ Cl F H H H C ₂ H ₅ Cl F H H H nC ₃ H ₇ Cl F H H H nC ₄ H ₉ Cl F H H H nc ₅ H ₁₁ Cl F H H H nc ₆ H ₁₃ Cl F H H H H Cl F F H H CH ₃ Cl F F H H C ₂ H ₅ Cl F F H H nC ₃ H ₇ Cl F F H H nC ₄ H ₉ Cl F F H H nc ₅ H ₁₁ Cl F F H H nc ₆ H ₁₃ Cl F F H H H OCF ₃ H H H H CH ₃ OCF ₃ H H H H C ₂ H ₅ OCF ₃ H H H H nC ₃ H ₇ OCF ₃ H H H H nC ₄ H ₉ OCF ₃ H H H H nc ₅ H ₁₁ OCF ₃ H H H H nc ₆ H ₁₃ OCF ₃ H H H H H OCF ₃ F H H H CH ₃ OCF ₃ F H H H C ₂ H ₅ OCF ₃ F H H H nC ₃ H ₇ OCF ₃ F H H H nC ₄ H ₉ OCF ₃ F H H H nc ₅ H ₁₁ OCF ₃ F H H H nc ₆ H ₁₃ OCF ₃ F H H H H OCF ₃ F F H H CH ₃ OCF ₃ F F H H C ₂ H ₅ OCF ₃ F F H H nC ₃ H ₇ OCF ₃ F F H H nC ₄ H ₉ OCF ₃ F F H H nc ₅ H ₁₁ OCF ₃ F F H H nc ₆ H ₁₃ OCF ₃ F F H H H OCHF ₂ H H H H CH ₃ OCHF ₂ H H H H C ₂ H ₅ OCHF ₂ H H H H nC ₃ H ₇ OCHF ₂ H H H H nC ₄ H ₉ OCHF ₂ H H H H nc ₅ H ₁₁ OCHF ₂ H H H H nc ₆ H ₁₃ OCHF ₂ H H H H H OCHF ₂ F H H H CH ₃ OCHF ₂ F H H H C ₂ H ₅ OCHF ₂ F H H H nC ₃ H ₇ OCHF ₂ F H H H nC ₄ H ₉ OCHF ₂ F H H H nc ₅ H ₁₁ OCHF ₂ F H H H nc ₆ H ₁₃ OCHF ₂ F H H H H OCHF ₂ F F H H CH ₃ OCHF ₂ F F H H C ₂ H ₅ OCHF ₂ F F H H nC ₃ H ₇ OCHF ₂ F F H H nC ₄ H ₉ OCHF ₂ F F H H nc ₅ H ₁₁ OCHF ₂ F F H H nc ₆ H ₁₃ OCHF ₂ F F H H H OCHFCF ₃ H H H H CH ₃ OCHFCF ₃ H H H H C ₂ H ₅ OCHFCF ₃ H H H H nC ₃ H ₇ OCHFCF ₃ H H H H nC ₄ H ₉ OCHFCF ₃ H H H H nc ₅ H ₁₁ OCHFCF ₃ H H H H nc ₆ H ₁₃ OCHFCF ₃ H H H H H OCHFCF ₃ F H H H CH ₃ OCHFCF ₃ F H H H C ₂ H ₅ OCHFCF ₃ F H H H nC ₃ H ₇ OCHFCF ₃ F H H H nC ₄ H ₉ OCHFCF ₃ F H H H nc ₅ H ₁₁ OCHFCF ₃ F H H H nc ₆ H ₁₃ OCHFCF ₃ F H H H H OCHFCF ₃ F F H H CH ₃ OCHFCF ₃ F F H H C ₂ H ₅ OCHFCF ₃ F F H H nC ₃ H ₇ OCHFCF ₃ F F H H nC ₄ H ₉ OCHFCF ₃ F F H H nc ₅ H ₁₁ OCHFCF ₃ F F H H nc ₆ H ₁₃ OCHFCF ₃ F F H H H OCHFCF ₃ H H H H CH ₃ OCHFCF ₃ H H H H C ₂ H ₅ OCHFCF ₃ H H H H nC ₃ H ₇ OCHFCF ₃ H H H H nC ₄ H ₉ OCHFCF ₃ H H H H nc ₅ H ₁₁ OCHFCF ₃ H H H H nc ₆ H ₁₃ OCHFCF ₃ H H H H H OCHFCF ₃ F H H H CH ₃ OCHFCF ₃ F H H H C ₂ H ₅ OCHFCF ₃ F H H H nC ₃ H ₇ OCHFCF ₃ F H H H nC ₄ H ₉ OCHFCF ₃ F H H H nc ₅ H ₁₁ OCHFCF ₃ F H H H nc ₆ H ₁₃ OCHFCF ₃ F H H H H OCHFCF ₃ F F H H CH ₃ OCHFCF ₃ F F H H C ₂ H ₅ OCHFCF ₃ F F H H nC ₃ H ₇ OCHFCF ₃ F F H H nC ₄ H ₉ OCHFCF ₃ F F H H nc ₅ H ₁₁ OCHFCF ₃ F F H H nc ₆ H ₁₃ OCHFCF ₃ F F H H H OCF ₂ CHFCF ₃ H H H H CH ₃ OCF ₂ CHFCF ₃ H H H H C ₂ H ₅ OCF ₂ CHFCF ₃ H H H H nC ₃ H ₇ OCF ₂ CHFCF ₃ H H H H nC ₄ H ₉ OCF ₂ CHFCF ₃ H H H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H H H H OCF ₂ CHFCF ₃ F H H H CH ₃ OCF ₂ CHFCF ₃ F H H H C ₂ H ₅ OCF ₂ CHFCF ₃ F H H H nC ₃ H ₇ OCF ₂ CHFCF ₃ F H H H nC ₄ H ₉ OCF ₂ CHFCF ₃ F H H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H H H H OCF ₂ CHFCF ₃ F F H H CH ₃ OCF ₂ CHFCF ₃ F F H H C ₂ H ₅ OCF ₂ CHFCF ₃ F F H H nC ₃ H ₇ OCF ₂ CHFCF ₃ F F H H nC ₄ H ₉ OCF ₂ CHFCF ₃ F F H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F H H H NCS H H H H CH ₃ NCS H H H H C ₂ H ₅ NCS H H H H nC ₃ H ₇ NCS H H H H nC ₄ H ₉ NCS H H H H nc ₅ H ₁₁ NCS H H H H nc ₆ H ₁₃ NCS H H H H H NCS F H H H CH ₃ NCS F H H H C ₂ H ₅ NCS F H H H nC ₃ H ₇ NCS F H H H nC ₄ H ₉ NCS F H H H nc ₅ H ₁₁ NCS F H H H nc ₆ H ₁₃ NCS F H H H H NCS F F H H CH ₃ NCS F F H H C ₂ H ₅ NCS F F H H nC ₃ H ₇ NCS F F H H nC ₄ H ₉ NCS F F H H nc ₅ H ₁₁ NCS F F H H nc ₆ H ₁₃ NCS F F H H H C ₂ F ₅ H H H H CH ₃ C ₂ F ₅ H H H H C ₂ H ₅ C ₂ F ₅ H H H H nC ₃ H ₇ C ₂ F ₅ H H H H nC ₄ H ₉ C ₂ F ₅ H H H H nc ₅ H ₁₁ C ₂ F ₅ H H H H nc ₆ H ₁₃ C ₂ F ₅ H H H H H C ₂ F ₅ F H H H CH ₃ C ₂ F ₅ F H H H C ₂ H ₅ C ₂ F ₅ F H H H nC ₃ H ₇ C ₂ F ₅ F H H H nC ₄ H ₉ C ₂ F ₅ F H H H nc ₅ H ₁₁ C ₂ F ₅ F H H H nc ₆ H ₁₃ C ₂ F ₅ F H H H H C ₂ F ₅ F F H H CH ₃ C ₂ F ₅ F F H H C ₂ H ₅ C ₂ F ₅ F F H H nC ₃ H ₇ C ₂ F ₅ F F H H nC ₄ H ₉ C ₂ F ₅ F F H H nc ₅ H ₁₁ C ₂ F ₅ F F H H nc ₆ H ₁₃ C ₂ F ₅ F F H H H C ₃ F ₇ H H H H CH ₃ C ₃ F ₇ H H H H C ₂ H ₅ C ₃ F ₇ H H H H nC ₃ H ₇ C ₃ F ₇ H H H H nC ₄ H ₉ C ₃ F ₇ H H H H nc ₅ H ₁₁ C ₃ F ₇ H H H H nc ₆ H ₁₃ C ₃ F ₇ H H H H H C ₃ F ₇ F H H H CH ₃ C ₃ F ₇ F H H H C ₂ H ₅ C ₃ F ₇ F H H H nC ₃ H ₇ C ₃ F ₇ F H H H nC ₄ H ₉ C ₃ F ₇ F H H H nc ₅ H ₁₁ C ₃ F ₇ F H H H nc ₆ H ₁₃ C ₃ F ₇ F H H H H C ₃ F ₇ F F H H CH ₃ C ₃ F ₇ F F H H C ₂ H ₅ C ₃ F ₇ F F H H nC ₃ H ₇ C ₃ F ₇ F F H H nC ₄ H ₉ C ₃ F ₇ F F H H nc ₅ H ₁₁ C ₃ F ₇ F F H H nc ₆ H ₁₃ C ₃ F ₇ F F H H H SF ₅ H H H H CH ₃ SF ₅ H H H H C ₂ H ₅ SF ₅ H H H H nC ₃ H ₇ SF ₅ H H H H nC ₄ H ₉ SF ₅ H H H H nc ₅ H ₁₁ SF ₅ H H H H nc ₆ H ₁₃ SF ₅ H H H H H SF ₅ F H H H CH ₃ SF ₅ F H H H C ₂ H ₅ SF ₅ F H H H nC ₃ H ₇ SF ₅ F H H H nC ₄ H ₉ SF ₅ F H H H nc ₅ H ₁₁ SF ₅ F H H H nc ₆ H ₁₃ SF ₅ F H H H H SF ₅ F F H H CH ₃ SF ₅ F F H H C ₂ H ₅ SF ₅ F F H H nC ₃ H ₇ SF ₅ F F H H nC ₄ H ₉ SF ₅ F F H H nc ₅ H ₁₁ SF ₅ F F H H nc ₆ H ₁₃ SF ₅ F F H H H CN H H H H CH ₃ CN H H H H C ₂ H ₅ CN H H H H nC ₃ H ₇ CN H H H H nC ₄ H ₉ CN H H H H nc ₅ H ₁₁ CN H H H H nc ₆ H ₁₃ CN H H H H H CN F H H H CH ₃ CN F H H H C ₂ H ₅ CN F H H H nC ₃ H ₇ CN F H H H nC ₄ H ₉ CN F H H H nc ₅ H ₁₁ CN F H H H nc ₆ H ₁₃ CN F H H H H CN F F H H CH ₃ CN F F H H C ₂ H ₅ CN F F H H nC ₃ H ₇ CN F F H H nC ₄ H ₉ CN F F H H nc ₅ H ₁₁ CN F F H H nc ₆ H ₁₃ CN F F H H H F H H F H CH ₃ F H H F H C ₂ H ₅ F H H F H C ₃ H ₇ F H H F H nC ₄ H ₉ F H H F H nc ₅ H ₁₁ F H H F H nc ₆ H ₁₃ F H H F H H F F H F H CH ₃ F F H F H C ₂ H ₅ F F H F H nC ₃ H ₇ F F H F H nC ₄ H ₉ F F H F H nc ₅ H ₁₁ F F H F H nc ₆ H ₁₃ F F H F H H F F F F H CH ₃ F F F F H C ₂ H ₅ F F F F H K 89 N (76,8) I, Δε = 29.9; Δn = 0.1310 nC ₃ H ₇ F F F F H K 70 N 102.3 I; Δε = 29.7; Δn = 0.1364 nC ₄ H ₉ F F F F H nc ₅ H ₁₁ F F F F H nc ₆ H ₁₃ F F F F H H Cl H H F H CH ₃ Cl H H F H C ₂ H ₅ Cl H H F H nC ₃ H ₇ Cl H H F H nC ₄ H ₉ Cl H H F H nc ₅ H ₁₁ Cl H H F H nc ₆ H ₁₃ Cl H H F H H Cl F H F H CH ₃ Cl F H F H C ₂ H ₅ Cl F H F H nC ₃ H ₇ Cl F H F H nC ₄ H ₉ Cl F H F H nc ₅ H ₁₁ Cl F H F H nc ₆ H ₁₃ Cl F H F H H Cl F F F H CH ₃ Cl F F F H C ₂ H ₅ Cl F F F H nC ₃ H ₇ Cl F F F H nC ₄ H ₉ Cl F F F H nc ₅ H ₁₁ Cl F F F H nc ₆ H ₁₃ Cl F F F H H OCF ₃ H H F H CH ₃ OCF ₃ H H F H C ₂ H ₅ OCF ₃ H H F H nC ₃ H ₇ OCF ₃ H H F H nC ₄ H ₉ OCF ₃ H H F H nc ₅ H ₁₁ OCF ₃ H H F H nc ₆ H ₁₃ OCF ₃ H H F H H OCF ₃ F H F H CH ₃ OCF ₃ F H F H C ₂ H ₅ OCF ₃ F H F H nC ₃ H ₇ OCF ₃ F H F H nC ₄ H ₉ OCF ₃ F H F H nC ₅ H11 OCF ₃ F H F H nc ₆ H ₁₃ OCF ₃ F H F H H OCF ₃ F F F H CH ₃ OCF ₃ F F F H C ₂ H ₅ OCF ₃ F F F H nC ₃ H ₇ OCF ₃ F F F H nC ₄ H _s OCF ₃ F F F H nc ₅ H ₁₁ OCF ₃ F F F H nc ₆ H ₁₃ OCF ₃ F F F H H OCHF ₂ H H F H CH ₃ OCHF ₂ H H F H C ₂ H ₅ OCHF ₂ H H F H nC ₃ H ₇ OCHF ₂ H H F H nC ₄ H ₉ OCHF ₂ H H F H nc ₅ H ₁₁ OCHF ₂ H H F H nc ₆ H ₁₃ OCHF ₂ H H F H H OCHF ₂ F H F H CH ₃ OCHF ₂ F H F H C ₂ H ₅ OCHF ₂ F H F H nC ₃ H ₇ OCHF ₂ F H F H nC ₄ H ₉ OCHF ₂ F H F H nc ₅ H ₁₁ OCHF ₂ F H F H nc ₆ H ₁₃ OCHF ₂ F H F H H OCHF ₂ F F F H CH ₃ OCHF ₂ F F F H C ₂ H ₅ OCHF ₂ F F F H nC ₃ H ₇ OCHF ₂ F F F H nC ₄ H ₉ OCHF ₂ F F F H nc ₅ H ₁₁ OCHF ₂ F F F H nc ₆ H ₁₃ OCHF ₂ F F F H H OCHFCF ₃ H H F H CH ₃ OCHFCF ₃ H H F H C ₂ H ₅ OCHFCF ₃ H H F H nC ₃ H ₇ OCHFCF ₃ H H F H nC ₄ H ₉ OCHFCF ₃ H H F H nc ₅ H ₁₁ OCHFCF ₃ H H F H nc ₆ H ₁₃ OCHFCF ₃ H H F H H OCHFCF ₃ F H F H CH ₃ OCHFCF ₃ F H F H C ₂ H ₅ OCHFCF ₃ F H F H nC ₃ H ₇ OCHFCF ₃ F H F H nC ₄ H ₉ OCHFCF ₃ F H F H nc ₅ H ₁₁ OCHFCF ₃ F H F H nc ₆ H ₁₃ OCHFCF ₃ F H F H H OCHFCF ₃ F F F H CH ₃ OCHFCF ₃ F F F H C ₂ H ₅ OCHFCF ₃ F F F H nC ₃ H ₇ OCHFCF ₃ F F F H nC ₄ H ₉ OCHFCF ₃ F F F H nc ₅ H ₁₁ OCHFCF ₃ F F F H nc ₆ H ₁₃ OCHFCF ₃ F F F H H OCHFCF ₃ H H F H CH ₃ OCHFCF ₃ H H F H C ₂ H ₅ OCHFCF ₃ H H F H nC ₃ H ₇ OCHFCF ₃ H H F H nC ₄ H ₉ OCHFCF ₃ H H F H nc ₅ H ₁₁ OCHFCF ₃ H H F H nc ₆ H ₁₃ OCHFCF ₃ H H F H H OCHFCF ₃ F H F H CH ₃ OCHFCF ₃ F H F H C ₂ H ₅ OCHFCF ₃ F H F H nC ₃ H ₇ OCHFCF ₃ F H F H nC ₄ H ₉ OCHFCF ₃ F H F H nc ₅ H ₁₁ OCHFCF ₃ F H F H nc ₆ H ₁₃ OCHFCF ₃ F H F H H OCHFCF ₃ F F F H CH ₃ OCHFCF ₃ F F F H C ₂ H ₅ OCHFCF ₃ F F F H nC ₃ H ₇ OCHFCF ₃ F F F H nC ₄ H ₉ OCHFCF ₃ F F F H nc ₅ H ₁₁ OCHFCF ₃ F F F H nc ₆ H ₁₃ OCHFCF ₃ F F F H H OCF ₂ CHFCF ₃ H H F H CH ₃ OCF ₂ CHFCF ₃ H H F H C ₂ H ₅ OCF ₂ CHFCF ₃ H H F H nC ₃ H ₇ OCF ₂ CHFCF ₃ H H F H nC ₄ H ₉ OCF ₂ CHFCF ₃ H H F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H F H H OCF ₂ CHFCF ₃ F H F H CH ₃ OCF ₂ CHFCF ₃ F H F H C ₂ H ₅ OCF ₂ CHFCF ₃ F H F H nC ₃ H ₇ OCF ₂ CHFCF ₃ F H F H nC ₄ H ₉ OCF ₂ CHFCF ₃ F H F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H F H H OCF ₂ CHFCF ₃ F F F H CH ₃ OCF ₂ CHFCF ₃ F F F H C ₂ H ₅ OCF ₂ CHFCF ₃ F F F H nC ₃ H ₇ OCF ₂ CHFCF ₃ F F F H nC ₄ H ₉ OCF ₂ CHFCF ₃ F F F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F F H H NCS H H F H CH ₃ NCS H H F H C ₂ H ₅ NCS H H F H nC ₃ H ₇ NCS H H F H nC ₄ H ₉ NCS H H F H nc ₅ H ₁₁ NCS H H F H nc ₆ H ₁₃ NCS H H F H H NCS F H F H CH ₃ NCS F H F H C ₂ H ₅ NCS F H F H nC ₃ H ₇ NCS F H F H nC ₄ H ₉ NCS F H F H nc ₅ H ₁₁ NCS F H F H nc ₆ H ₁₃ NCS F H F H H NCS F F F H CH ₃ NCS F F F H C ₂ H ₅ NCS F F F H nC ₃ H ₇ NCS F F F H nC ₄ H ₉ NCS F F F H nc ₅ H ₁₁ NCS F F F H nc ₆ H ₁₃ NCS F F F H H C ₂ F ₅ H H F H CH ₃ C ₂ F ₅ H H F H C ₂ H ₅ C ₂ F ₅ H H F H nC ₃ H ₇ C ₂ F ₅ H H F H nC ₄ H ₉ C ₂ F ₅ H H F H nc ₅ H ₁₁ C ₂ F ₅ H H F H nc ₆ H ₁₃ C ₂ F ₅ H H F H H C ₂ F ₅ F H F H CH ₃ C ₂ F ₅ F H F H C ₂ H ₅ C ₂ F ₅ F H F H nC ₃ H ₇ C ₂ F ₅ F H F H nC ₄ H ₉ C ₂ F ₅ F H F H nc ₅ H ₁₁ C ₂ F ₅ F H F H nc ₆ H ₁₃ C ₂ F ₅ F H F H H C ₂ F ₅ F F F H CH ₃ C ₂ F ₅ F F F H C ₂ H ₅ C ₂ F ₅ F F F H nC ₃ H ₇ C ₂ F ₅ F F F H n-C4H9 C ₂ F ₅ F F F H nc ₅ H ₁₁ C ₂ F ₅ F F F H nc ₆ H ₁₃ C ₂ F ₅ F F F H H C ₃ F ₇ H H F H CH ₃ C ₃ F ₇ H H F H C ₂ H ₅ C ₃ F ₇ H H F H nC ₃ H ₇ C ₃ F ₇ H H F H nC ₄ H ₉ C ₃ F ₇ H H F H nc ₅ H ₁₁ C ₃ F ₇ H H F H nc ₆ H ₁₃ C ₃ F ₇ H H F H H C ₃ F ₇ F H F H CH ₃ C ₃ F ₇ F H F H C ₂ H ₅ C ₃ F ₇ F H F H nC ₃ H ₇ C ₃ F ₇ F H F H nC ₄ H ₉ C ₃ F ₇ F H F H nc ₅ H ₁₁ C ₃ F ₇ F H F H nc ₆ H ₁₃ C ₃ F ₇ F H F H H C ₃ F ₇ F F F H CH ₃ C ₃ F ₇ F F F H C ₂ H ₅ C ₃ F ₇ F F F H nC ₃ H ₇ C ₃ F ₇ F F F H nC ₄ H ₉ C ₃ F ₇ F F F H nc ₅ H ₁₁ C ₃ F ₇ F F F H nc ₆ H ₁₃ C ₃ H ₇ F F F H H SF ₅ H H F H CH ₃ SF ₅ H H F H C ₂ H ₅ SF ₅ H H F H nC ₃ H ₇ SF ₅ H H F H nC ₄ H ₉ SF ₅ H H F H nc ₅ H ₁₁ SF ₅ H H F H nc ₆ H ₁₃ SF ₅ H H F H H SF ₅ F H F H CH ₃ SF ₅ F H F H C ₂ H ₅ SF ₅ F H F H nC ₃ H ₇ SF ₅ F H F H nC ₄ H ₉ SF ₅ F H F H nc ₅ H ₁₁ SF ₅ F H F H nc ₆ H ₁₃ SF ₅ F H F H H SF ₅ F F F H CH ₃ SF ₅ F F F H C ₂ H ₅ SF ₅ F F F H nC ₃ H ₇ SF ₅ F F F H nC ₄ H ₉ SF ₅ F F F H nc ₅ H ₁₁ SF ₅ F F F H nc ₆ H ₁₃ SF ₅ F F F H H CN H H F H CH ₃ CN H H F H C ₂ H ₅ CN H H F H nC ₃ H ₇ CN H H F H nC ₄ H ₉ CN H H F H nc ₅ H ₁₁ CN H H F H nc ₆ H ₁₃ CN H H F H H CN F H F H CH ₃ CN F H F H C ₂ H ₅ CN F H F H nC ₃ H ₇ CN F H F H nC ₄ H ₉ CN F H F H nc ₅ H ₁₁ CN F H F H nc ₆ H ₁₃ CN F H F H H CN F F F H CH ₃ CN F F F H C ₂ H ₅ CN F F F H nC ₃ H ₇ CN F F F H nC ₄ H ₉ CN F F F H nc ₅ H ₁₁ CN F F F H nc ₆ H ₁₃ CN F F F H H F H H F F CH ₃ F H H F F C ₂ H ₅ F H H F F nC ₄ H ₉ F H H F F nc ₅ H ₁₁ F H H F F nc ₆ H ₁₃ F H H F F HF F F H F F CH ₃ F F H F F C ₂ H ₅ F F H F F nC ₃ H ₇ F F H F F nC ₄ H ₉ F F H F F nc ₅ H ₁₁ F F H F F nc ₆ H ₁₃ F F H F F H F F F F F CH ₃ F F F F F C ₂ H ₅ F F F F F C ₂ H ₅ F F F F F K 91 N (58.8) I; Δε = 35, 0; Δn = 0.1149 nC ₃ H ₇ F F F F F K 83 N (83.0) I; Δε = 34.9; Δn = 0.1231 nC ₄ H ₉ F F F F F K 90 N 79.4 I; Δε = 32.4; Δn = 0.1171 nc ₅ H ₁₁ F F F F F K 82 N 84.3 I; Δε = 31.9; Δn = 0.1205 nc ₆ H ₁₃ F F F F F K 89 N (83.4) I; Δε = 30.6; Δn = 0.1116 nC ₇ H ₁₅ F F F F F K 82 N 84.3 I; Δε = 30.3; Δn = 0.1130 H Cl H H F F CH ₃ Cl H H F F C ₂ H ₅ Cl H H F F nC ₃ H ₇ Cl H H F F nC ₄ H ₉ Cl H H F F nc ₅ H ₁₁ Cl H H F F nc ₆ H ₁₃ Cl H H F F H Cl F H F F CH ₃ Cl F H F F C ₂ H ₅ Cl F H F F nC ₃ H ₇ Cl F H F F nC ₄ H ₉ Cl F H F F nc ₅ H ₁₁ Cl F H F F nc ₆ H ₁₃ Cl F H F F H Cl F F F F CH ₃ Cl F F F F C ₂ H ₅ Cl F F F F nC ₃ H ₇ Cl F F F F K 80 N 106.7 I; Δε = 31.5; Δn = 0.1372 nC ₄ H ₉ Cl F F F F nc ₅ H ₁₁ Cl F F F F nc ₆ H ₁₃ Cl F F F F H OCF ₃ H H F F CH ₃ OCF ₃ H H F F C ₂ H ₅ OCF ₃ H H F F nC ₃ H ₇ OCF ₃ H H F F K 80 N 119.8 I; Δε = 25.3; Δn = 0.1330 nC ₄ H ₉ OCF ₃ H H F F nc ₅ H ₁₁ OCF ₃ H H F F nc ₆ H ₁₃ OCF ₃ H H F F H OCF ₃ F H F F CH ₃ OCF ₃ F H F F C ₂ H ₅ OCF ₃ F H F F nC ₃ H ₇ OCF ₃ F H F F K 48 S _A (46) N 105.1 I; Δε = 29.8; An = 0.1180 nC ₄ H ₉ OCF ₃ F H F F nc ₅ H ₁₁ OCF ₃ F H F F nc ₆ H ₁₃ OCF ₃ F H F F H OCF ₃ F F F F CH ₃ OCF ₃ F F F F C ₂ H ₅ OCF ₃ F F F F nC ₃ H ₇ OCF ₃ F F F F K 73 N 97.5 I; Δε = 35.6; Δn = 0.1158 nC ₄ H ₉ OCF ₃ F F F F nc ₅ H ₁₁ OCF ₃ F F F F nc ₆ H ₁₃ OCF ₃ F F F F H OCHF ₂ H H F F CH ₃ OCHF ₂ H H F F C ₂ H ₅ OCHF ₂ H H F F nC ₃ H ₇ OCHF ₂ H H F F nC ₄ H ₉ OCHF ₂ H H F F nc ₅ H ₁₁ OCHF ₂ H H F F nc ₆ H ₁₃ OCHF ₂ H H F F H OCHF ₂ F H F F CH ₃ OCHF ₂ F H F F C ₂ H ₅ OCHF ₂ F H F F nC ₃ H ₇ OCHF ₂ F H F F nC ₄ H ₉ OCHF ₂ F H F F nc ₅ H ₁₁ OCHF ₂ F H F F nc ₆ H ₁₃ OCHF ₂ F H F F H OCHF ₂ F F F F CH ₃ OCHF ₂ F F F F C ₂ H ₅ OCHF ₂ F F F F nC ₃ H ₇ OCHF ₂ F F F F nC ₄ H ₉ OCHF ₂ F F F F nc ₅ H ₁₁ OCHF ₂ F F F F nc ₆ H ₁₃ OCHF ₂ F F F F H OCHFCF ₃ H H F F CH ₃ OCHFCF ₃ H H F F C ₂ H ₅ OCHFCF ₃ H H F F nC ₃ H ₇ OCHFCF ₃ H H F F nC ₄ H ₉ OCHFCF ₃ H H F F nc ₅ H ₁₁ OCHFCF ₃ H H F F nc ₆ H ₁₃ OCHFCF ₃ H H F F H OCHFCF ₃ F H F F CH ₃ OCHFCF ₃ F H F F C ₂ H ₅ OCHFCF ₃ F H F F nC ₃ H ₇ OCHFCF ₃ F H F F nC ₄ H ₉ OCHFCF ₃ F H F F nc ₅ H ₁₁ OCHFCF ₃ F H F F nc ₆ H ₁₃ OCHFCF ₃ F H F F H OCHFCF ₃ F F F F CH ₃ OCHFCF ₃ F F F F C ₂ H ₅ OCHFCF ₃ F F F F nC ₃ H ₇ OCHFCF ₃ F F F F nC ₄ H ₉ OCHFCF ₃ F F F F nc ₅ H ₁₁ OCHFCF ₃ F F F F nc ₆ H ₁₃ OCHFCF ₃ F F F F H OCHFCF ₃ H H F F CH ₃ OCHFCF ₃ H H F F C ₂ H ₅ OCHFCF ₃ H H F F nC ₃ H ₇ OCHFCF ₃ H H F F nC ₄ H ₉ OCHFCF ₃ H H F F nc ₅ H ₁₁ OCHFCF ₃ H H F F nc ₆ H ₁₃ OCHFCF ₃ H H F F H OCHFCF ₃ F H F F CH ₃ OCHFCF ₃ F H F F C ₂ H ₅ OCHFCF ₃ F H F F nC ₃ H ₇ OCHFCF ₃ F H F F nC ₄ H ₉ OCHFCF ₃ F H F F nc ₅ H ₁₁ OCHFCF ₃ F H F F nc ₆ H ₁₃ OCHFCF ₃ F H F F H OCHFCF ₃ F F F F CH ₃ OCHFCF ₃ F F F F C ₂ H ₅ OCHFCF ₃ F F F F nC ₃ H ₇ OCHFCF ₃ F F F F nC ₄ H ₉ OCHFCF ₃ F F F F nc ₅ H ₁₁ OCHFCF ₃ F F F F nc ₆ H ₁₃ OCHFCF ₃ F F F F H OCF ₂ CHFCF ₃ . H H F F CH ₃ OCF ₂ CHFCF ₃ H H F F C ₂ H ₅ OCF ₂ CHFCF ₃ H H F F nC ₃ H ₇ OCF ₂ CHFCF ₃ H H F F nC ₄ H ₉ OCF ₂ CHFCF ₃ H H F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H F F H OCF ₂ CHFCF ₃ F H F F CH ₃ OCF ₂ CHFCF ₃ F H F F C ₂ H ₅ OCF ₂ CHFCF ₃ F H F F nC ₃ H ₇ OCF ₂ CHFCF ₃ F H F F nC ₄ H ₉ OCF ₂ CHFCF ₃ F H F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H F F H OCF ₂ CHFCF ₃ F F F F CH ₃ OCF ₂ CHFCF ₃ F F F F C ₂ H ₅ OCF ₂ CHFCF ₃ F F F F nC ₃ H ₇ OCF ₂ CHFCF ₃ F F F F nC ₄ H ₉ OCF ₂ CHFCF ₃ F F F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F F F H NCS H H F F CH ₃ NCS H H F F C ₂ H ₅ NCS H H F F nC ₃ H ₇ NCS H H F F K 107 N 185.5 I; Δε = 31.4; Δn = 0.2052 nC ₄ H ₉ NCS H H F F nc ₅ H ₁₁ NCS H H F F nc ₆ H ₁₃ NCS H H F F H NCS F H F F CH ₃ NCS F H F F C ₂ H ₅ NCS F H F F nC ₃ H ₇ NCS F H F F nC ₄ H ₉ NCS F H F F nc ₅ H ₁₁ NCS F H F F nc ₆ H ₁₃ NCS F H F F H NCS F F F F CH ₃ NCS F F F F C ₂ H ₅ NCS F F F F nC ₃ H ₇ NCS F F F F nC ₄ H ₉ NCS F F F F nc ₅ H ₁₁ NCS F F F F nc ₆ H ₁₃ NCS F F F F H C ₂ F ₅ H H F F CH ₃ C ₂ F ₅ H H F F C ₂ H ₅ C ₂ F ₅ H H F F nC ₃ H ₇ C ₂ F ₅ H H F F nC ₄ H ₉ C ₂ F ₅ H H F F nc ₅ H ₁₁ C ₂ F ₅ H H F F nc ₆ H ₁₃ C ₂ F ₅ H H F F H C ₂ F ₅ F H F F CH ₃ C ₂ F ₅ F H F F C ₂ H ₅ C ₂ F ₅ F H F F nC ₃ H ₇ C ₂ F ₅ F H F F nC ₄ H ₉ C ₂ F ₅ F H F F nc ₅ H ₁₁ C ₂ F ₅ F H F F nc ₆ H ₁₃ C ₂ F ₅ F H F F H C ₂ F ₅ F F F F CH ₃ C ₂ F ₅ F F F F C ₂ H ₅ C ₂ F ₅ F F F F nC ₃ H ₇ C ₂ F ₅ F F F F nC ₄ H ₉ C ₂ F ₅ F F F F nc ₅ H ₁₁ C ₂ F ₅ F F F F nc ₆ H ₁₃ C ₂ F ₅ F F F F H C ₃ F ₇ H H F F CH ₃ C ₃ F ₇ H H F F C ₂ H ₅ C ₃ F ₇ H H F F nC ₃ H ₇ C ₃ F ₇ H H F F nC ₄ H ₉ C ₃ F ₇ H H F F nc ₅ H ₁₁ C ₃ F ₇ H H F F nc ₆ H ₁₃ C ₃ F ₇ H H F F H C ₃ F ₇ F H F F CH ₃ C ₃ F ₇ F H F F C ₂ H ₅ C ₃ F ₇ F H F F nC ₃ H ₇ C ₃ F ₇ F H F F nC ₄ H ₉ C ₃ F ₇ F H F F nc ₅ H ₁₁ C ₃ F ₇ F H F F nc ₆ H ₁₃ C ₃ F ₇ F H F F H C ₃ F ₇ F F F F CH ₃ C ₃ F ₇ F F F F C ₂ H ₅ C ₃ F ₇ F F F F nC ₃ H ₇ C ₃ F ₇ F F F F nC ₄ H ₉ C ₃ F ₇ F F F F nc ₅ H ₁₁ C ₃ F ₇ F F F F nc ₆ H ₁₃ C ₃ F ₇ F F F F H SF ₅ H H F F CH ₃ SF ₅ H H F F C ₂ H ₅ SF ₅ H H F F nC ₃ H ₇ SF ₅ H H F F nC ₄ H ₉ SF ₅ H H F F nc ₅ H ₁₁ SF ₅ H H F F nc ₆ H ₁₃ SF ₅ H H F F H SF ₅ F H F F CH ₃ SF ₅ F H F F C ₂ H ₅ SF ₅ F H F F nC ₃ H ₇ SF ₅ F H F F nC ₄ H ₉ SF ₅ F H F F nc ₅ H ₁₁ SF ₅ F H F F nc ₆ H ₁₃ SF ₅ F H F F H SF ₅ F F F F CH ₃ SF ₅ F F F F C ₂ H ₅ SF ₅ F F F F nC ₃ H ₇ SF ₅ F F F F K 110 N (83.4) I; △ ε = 33.8; Δn = 0.121 l nC ₄ H ₉ SF ₅ F F F F nc ₅ H ₁₁ SF ₅ F F F F nc ₆ H ₁₃ SF ₅ F F F F H CN H H F F CH ₃ CN H H F F C ₂ H ₅ CN H H F F nC ₃ H ₇ CN H H F F nC ₄ H ₉ CN H H F F nc ₅ H ₁₁ CN H H F F nc ₆ H ₁₃ CN H H F F H CN F H F F CH ₃ CN F H F F C ₂ H ₅ CN F H F F nC ₃ H ₇ CN F H F F nC ₄ H ₉ CN F H F F nc ₅ H ₁₁ CN F H F F nc ₆ H ₁₃ CN F H F F H CN F F F F CH ₃ CN F F F F C ₂ H ₅ CN F F F F K 98 N _Re (71) Sc (84) N 127.6I Δs = 67.8; = N = 0.1445 nC ₃ H ₇ CN F F F F K 75 S _c ? (65) N 144.1 I Δn = 0.1561; As = 66.5 nC ₄ H ₉ CN F F F F K 79 N 139.3 I; Δε = 64.2; Δn = 0.1477 nc ₅ H ₁₁ CN F F F F K 65 S _c (44) N 141.5 I; Δε = 61.8; = N = 0.1490 nc ₆ H ₁₃ CN F F F F nC ₇ H ₁₅ CN F F F F K 51 N 130.8 I; Δε = 58.4; = N = 0.1445 H CF ₃ H H F F C ₂ Hs CF ₃ H H F F nC ₃ H ₇ CF ₃ H H F F K 95 N (87.5) I; Δε = 31.5; = N = 0.1330 nC ₄ H ₉ CF ₃ H H F F nc ₅ H ₁₁ CF ₃ H H F F nc ₆ H ₁₃ CF ₃ H H F F CH ₂ = CH CF ₃ H H F F H CF ₃ F F F F C ₂ H ₅ CF ₃ F F F F nC ₃ H ₇ CF ₃ F F F F K 91 I; Δn = 0.1190; Δε = 40.8 nC ₄ H ₉ CF ₃ F F F F nc ₅ H ₁₁ CF ₃ F F F F nc ₆ H ₁₃ CF ₃ F F F F CH ₂ = CH CF ₃ F F F F H F H H F F C ₂ H ₅ F H H F F nC ₃ H ₇ F H H F F nC ₄ H ₉ F H H F F nc ₅ H ₁₁ F H H F F nc ₆ H ₁₃ F H H F F CH ₂ = CH F H H F F

Example 3

Step 3.1

A solution of 61.2 mmol L in 500 ml CH ₂ Cl ₂ is added dropwise at -20 ° C with 62.7 mmol trifluoromethanesulfonic acid. It is allowed to come to room temperature for 30 minutes and then cooled to -70 ° C. Now, first a solution of 91 mmol of 4-bromo-3-fluorophenol and 101 mmol of triethylamine in 200 ml of CH ₂ Cl ₂ , 5 min later added 310 mmol of triethylamine tris (hydrofluoride). After a further 5 minutes, a suspension of 315 mmol of 1,3-dibromo-5,5-dimethylhydanthoin is added in small portions and the mixture is stirred at -70 ° C. for a further 1 h. It is allowed to -10 ° C come and pour the reaction mixture into ice-cold NaOH. The reaction is carried out as usual in water and the crude product is purified by chromatography on silica gel (heptane / MTB ether 4: 1) and crystallization from ethanol at -20 ° C.

Step 3.2

A mixture of 50 mmol of M , 50 mmol of 3,4,5-trifluorobenzeneboronic acid, 2.5 mmol of Pd (PPh ₃ ) ₄ , 300 ml of toluene and 300 ml of Na borate buffer (pH = 9) is stirred at 80 ° C. for 18 h , The mixture is poured into 500 ml of 0.1 N HCl, the product is extracted with CH ₂ Cl ₂ , dried over Na ₂ SO ₄ and rotated to dryness. The crude product is chromatographed on silica gel in n-heptane and then recrystallized from n-heptane at -20 ° C. K 61 N 191.8 I; Δn = 0.1220; Δε = 19.1

hergestellt: R¹ X L¹ L² H F H H CH₃ F H H C₂H₅ F H H n-C₃H₇ F H H K 84 N 232,4 I; Δε = 9,4; Δn = 0,1390 n-C₄H₉ F H H n-C₅H₁₁ F H H n-C₆H₁₃ F H H H F F H CH₃ F F H C₂H₅ F F H n-C₃H₇ F F H K 44 S_M? 45 N 212,6 I; Δε = 13,4; Δn = 0,1328 n-C₄H₉ F F H n-C₅H₁₁ F F H n-C₆H₁₃ F F H H F F F CH₃ F F F C₂H₅ F F F n-C₄H₉ F F F n-C₅H₁₁ F F F n-C₆H₁₃ F F F H Cl H H CH₃ Cl H H C₂H₅ Cl H H n-C₃H₇ Cl H H n-C₄H₉ Cl H H n-C₅H₁₁ Cl H H n-C₆H₁₃ Cl H H H Cl F H CH₃ Cl F H C₂H₅ Cl F H n-C₃H₇ Cl F H n-C₄H₉ Cl F H n-C₅H₁₁ Cl F H n-C₆H₁₃ Cl F H H Cl F F CH₃ Cl F F C₂H₅ Cl F F n-C₃H₇ Cl F F n-C₄H₉ Cl F F n-C₅H₁₁ Cl F F n-C₆H₁₃ Cl F F H OCF₃ H H CH₃ OCF₃ H H C₂H₅ OCF₃ H H n-C₃H₇ OCF₃ H H n-C₄H₉ OCF₃ H H n-C₅H₁₁ OCF₃ H H n-C₆H₁₃ OCF₃ H H H OCF₃ F H CH₃ OCF₃ F H C₂H₅ OCF₃ F H n-C₃H₇ OCF₃ F H n-C₄H₉ OCF₃ F H n-C₅H₁₁ OCF₃ F H n-C₆H₁₃ OCF₃ F H H OCF₃ F F CH₃ OCF₃ F F C₂H₅ OCF₃ F F n-C₃H₇ OCF₃ F F n-C₄H₉ . OCF₃ F F n-C₅H₁₁ OCF₃ F F n-C₆H₁₃ OCF₃ F F H OCHF₂ H H CH₃ OCHF₂ H H C₂H₅ OCHF₂ H H n-C₃H₇ OCHF₂ H H n-C₄H₉ OCHF₂ H H n-C₅H₁₁ OCHF₂ H H n-C₆H₁₃ OCHF₂ H H H OCHF₂ F H CH₃ OCHF₂ F H C₂H₅ OCHF₂ F H n-C₃H₇ OCHF₂ F H n-C₄H₉ OCHF₂ F H n-C₅H₁₁ OCHF₂ F H n-C₆H₁₃ OCHF₂ F H H OCHF₂ F F CH₃ OCHF₂ F F C₂H₅ OCHF₂ F F n-C₃H₇ OCHF₂ F F n-C₄H₉ OCHF₂ F F n-C₅H₁₁ OCHF₂ F F n-C₆H₁₃ OCHF₂ F F H OCHFCF₃ H H CH₃ OCHFCF₃ H H C₂H₅ OCHFCF₃ H H n-C₃H₇ OCHFCF₃ H H n-C₄H₉ OCHFCF₃ H H n-C₅H₁₁ OCHFCF₃ H H n-C₆H₁₃ OCHFCF₃ H H H OCHFCF₃ F H CH₃ OCHFCF₃ F H C₂H₅ OCHFCF₃ F H n-C₃H₇ OCHFCF₃ F H n-C₄Hg OCHFCF₃ F H n-C₅H₁₁ OCHFCF₃ F H n-C₆H₁₃ OCHFCF₃ F H H OCHFCF₃ F F CH₃ OCHFCF₃ F F C₂Hs OCHFCF₃ F F n-C₃H₇ OCHFCF₃ F F n-C₄H₉ OCHFCF₃ F F n-C₅H₁₁ OCHFCF₃ F F n-C₆H₁₃ OCHFCF₃ F F H OCHFCF₃ H H CH₃ OCHFCF₃ H H C₂H₅ OCHFCF₃ H H n-C₃H₇ OCHFCF₃ H H n-C₄H₉ OCHFCF₃ H H n-C₅H₁₁ OCHFCF₃ H H n-C₆H₁₃ OCHFCF₃ H H H OCHFCF₃ F H CH₃ OCHFCF₃ F H C₂H₅ OCHFCF₃ F H n-C₃H₇ OCHFCF₃ F H n-C₄H₉ OCHFCF₃ F H n=C₅H₁₁ OCHFCF₃ F H n-C₆H₁₃ OCHFCF₃ F H H OCHFCF₃ F F CH₃ OCHFCF₃ F F C₂H₅ OCHFCF₃ F F n-C₃H₇ OCHFCF₃ F F n-C₄H₉ OCHFCF₃ F F n-C₅H₁₁ OCHFCF₃ F F n-C₆H₁₃ OCHFCF₃ F F H OCF₂CHFCF₃ H H CH₃ OCF₂CHFCF₃ H H C₂H₅ OCF₂CHFCF₃ H H n-C₃H₇ OCF₂CHFCF₃ H H n-C₄H₉ OCF₂CHFCF₃ H H n-C₅H₁₁ OCF₂CHFCF₃ H H n-C₆H₁₃ OCF₂CHFCF₃ H H H OCF₂CHFCF₃ F H CH₃ OCF₂CHFCF₃ F H C₂H₅ OCF₂CHFCF₃ F H n-C₃H₇ OCF₂CHFCF₃ F H n-C₄H₉ OCF₂CHFCF₃ F H n-C₅H₁₁ OCF₂CHFCF₃ F H n-C₆H₁₃ OCF₂CHFCF₃ F H H OCF₂CHFCF₃ F F CH₃ OCF₂CHFCF₃ F F C₂H₅ OCF₂CHFCF₃ F F n-C₃H₇ OCF₂CHFCF₃ F F n-C₄H₉ OCF₂CHFCF₃ F F n-C₅H₁₁ OCF₂CHFCF₃ F F n-C₆H₁₃ OCF₂CHFCF₃ F F H NCS H H CH₃ NCS H H C₂H₅ NCS H H n-C₃H₇ NCS H H n-C₄H₉ NCS H H n-C₅H₁₁ NCS H H n-C₆H₁₃ NCS H H H NCS F H CH₃ NCS F H C₂H₅ NCS F H n-C₃H₇ NCS F H n-C₄H₉ NCS F H n-C₅H₁₁ NCS F H n-C₆H₁₃ NCS F H H NCS F F CH₃ NCS F F C₂H₅ NCS F F n-C₃H₇ NCS F F n-C₄H₉ NCS F F n-C₅H₁₁ NCS F F n-C₆H₁₃ NCS F F H C₂F₅ H H CH₃ C₂F₅ H H C₂H₅ C₂F₅ H H n-C₃H₇ C₂F₅ H H n-C₄H₉ C₂F₅ H H n-C₅H₁₁ C₂F₅ H H n-C₆H₁₃ C₂F₅ H H H C₂F₅ F H CH₃ C₂F₅ F H C₂H₅ C₂F₅ F H n-C₃H₇ C₂F₅ F H n-C₄H₉ C₂F₅ F H n-C₅H₁₁ C₂F₅ F H n-C₆H₁₃ C₂F₅ F H H C₂F₅ F F CH₃ C₂F₅ F F C₂H₅ C₂F₅ F F n-C₃H₇ C₂F₅ F F n-C₄H₉ C₂F₅ F F n-C₅H₁₁ C₂F₅ F F n-C₆H₁₃ C₂F₅ F F H C₃F₇ H H CH₃ C₃F₇ H H C₂H₅ C₃F₇ H H n-C₃H₇ C₃F₇ H H n-C₄H₉ C₃F₇ H H n-C₅H₁₁ C₃F₇ H H n-C₆H₁₃ C₃F₇ H H H C₃F₇ F H CH₃ C₃F₇ F H C₂H₅ C₃F₇ F H _n-C3H7 C₃F₇ F H n-C₄H₉ C₃F₇ F H n-C₅H₁₁ C₃F₇ F H n-C₆H₁₃ C₃F₇ F H H C₃F₇ F F CH₃ C₃F₇ F F C₂H₅ C₃F₇ F F n-C₃H₇ C₃F₇ F F n-C₄H₉ C₃F₇ F F n-C₅H₁₁ C₃F₇ F F n-C₆H₁₃ C₃F₇ F F H SF₅ H H CH₃ SF₅ H H C₂H₅ SF₅ H H n-C₃H₇ SF₅ H H n-C₄H₉ SF₅ H H n-C₅H₁₁ SF₅ H H n-C₆H₁₃ SF₅ H H H SF₅ F H CH₃ SF₅ F H C₂H₅ SF₅ F H n-C₃H₇ SF₅ F H n-C₄H₉ SF₅ F H n-C₅H₁₁ SF₅ F H n-C₆H₁₃ SF₅ F H H SF₅ F F CH₃ SF₅ F F C₂H₅ SF₅ F F n-C₃H₇ SF₅ F F n-C₄H₉ SF₅ F F n-C₅H₁₁ SF₅ F F n-C₆H₁₃ SF₅ F F H CN H H CH₃ CN H H C₂H₅ CN H H n-C₃H₇ CN H H n-C₄H₉ CN H H n-C₅H₁₁ CN H H n-C₆H₁₃ CN H H H CN F H CH₃ CN F H C₂H₅ CN F H n-C₃H₇ CN F H n-C₄H₉ CN F H Analogously, the following compounds of the formula

produced: R ¹ X L ¹ L ² HF H H CH ₃ F H H C ₂ H ₅ F H H nC ₃ H ₇ F H H K 84 N 232.4 I; Δε = 9.4; Δn = 0.1390 nC ₄ H ₉ F H H nc ₅ H ₁₁ F H H nc ₆ H ₁₃ F H H H F F H CH ₃ F F H C ₂ H ₅ F F H nC ₃ H ₇ F F H K 44 S _M ? 45 N 212.6 I; Δε = 13.4; Δn = 0.1328 nC ₄ H ₉ F F H nc ₅ H ₁₁ F F H nc ₆ H ₁₃ F F H H F F F CH ₃ F F F C ₂ H ₅ F F F nC ₄ H ₉ F F F nc ₅ H ₁₁ F F F nc ₆ H ₁₃ F F F H Cl H H CH ₃ Cl H H C ₂ H ₅ Cl H H nC ₃ H ₇ Cl H H nC ₄ H ₉ Cl H H nc ₅ H ₁₁ Cl H H nc ₆ H ₁₃ Cl H H H Cl F H CH ₃ Cl F H C ₂ H ₅ Cl F H nC ₃ H ₇ Cl F H nC ₄ H ₉ Cl F H nc ₅ H ₁₁ Cl F H nc ₆ H ₁₃ Cl F H H Cl F F CH ₃ Cl F F C ₂ H ₅ Cl F F nC ₃ H ₇ Cl F F nC ₄ H ₉ Cl F F nc ₅ H ₁₁ Cl F F nc ₆ H ₁₃ Cl F F H OCF ₃ H H CH ₃ OCF ₃ H H C ₂ H ₅ OCF ₃ H H nC ₃ H ₇ OCF ₃ H H nC ₄ H ₉ OCF ₃ H H nc ₅ H ₁₁ OCF ₃ H H nc ₆ H ₁₃ OCF ₃ H H H OCF ₃ F H CH ₃ OCF ₃ F H C ₂ H ₅ OCF ₃ F H nC ₃ H ₇ OCF ₃ F H nC ₄ H ₉ OCF ₃ F H nc ₅ H ₁₁ OCF ₃ F H nc ₆ H ₁₃ OCF ₃ F H H OCF ₃ F F CH ₃ OCF ₃ F F C ₂ H ₅ OCF ₃ F F nC ₃ H ₇ OCF ₃ F F nC ₄ H ₉ , OCF ₃ F F nc ₅ H ₁₁ OCF ₃ F F nc ₆ H ₁₃ OCF ₃ F F H OCHF ₂ H H CH ₃ OCHF ₂ H H C ₂ H ₅ OCHF ₂ H H nC ₃ H ₇ OCHF ₂ H H nC ₄ H ₉ OCHF ₂ H H nc ₅ H ₁₁ OCHF ₂ H H nc ₆ H ₁₃ OCHF ₂ H H H OCHF ₂ F H CH ₃ OCHF ₂ F H C ₂ H ₅ OCHF ₂ F H nC ₃ H ₇ OCHF ₂ F H nC ₄ H ₉ OCHF ₂ F H nc ₅ H ₁₁ OCHF ₂ F H nc ₆ H ₁₃ OCHF ₂ F H H OCHF ₂ F F CH ₃ OCHF ₂ F F C ₂ H ₅ OCHF ₂ F F nC ₃ H ₇ OCHF ₂ F F nC ₄ H ₉ OCHF ₂ F F nc ₅ H ₁₁ OCHF ₂ F F nc ₆ H ₁₃ OCHF ₂ F F H OCHFCF ₃ H H CH ₃ OCHFCF ₃ H H C ₂ H ₅ OCHFCF ₃ H H nC ₃ H ₇ OCHFCF ₃ H H nC ₄ H ₉ OCHFCF ₃ H H nc ₅ H ₁₁ OCHFCF ₃ H H nc ₆ H ₁₃ OCHFCF ₃ H H H OCHFCF ₃ F H CH ₃ OCHFCF ₃ F H C ₂ H ₅ OCHFCF ₃ F H nC ₃ H ₇ OCHFCF ₃ F H nc ₄ Hg OCHFCF ₃ F H nc ₅ H ₁₁ OCHFCF ₃ F H nc ₆ H ₁₃ OCHFCF ₃ F H H OCHFCF ₃ F F CH ₃ OCHFCF ₃ F F C ₂ Hs OCHFCF ₃ F F nC ₃ H ₇ OCHFCF ₃ F F nC ₄ H ₉ OCHFCF ₃ F F nc ₅ H ₁₁ OCHFCF ₃ F F nc ₆ H ₁₃ OCHFCF ₃ F F H OCHFCF ₃ H H CH ₃ OCHFCF ₃ H H C ₂ H ₅ OCHFCF ₃ H H nC ₃ H ₇ OCHFCF ₃ H H nC ₄ H ₉ OCHFCF ₃ H H nc ₅ H ₁₁ OCHFCF ₃ H H nc ₆ H ₁₃ OCHFCF ₃ H H H OCHFCF ₃ F H CH ₃ OCHFCF ₃ F H C ₂ H ₅ OCHFCF ₃ F H nC ₃ H ₇ OCHFCF ₃ F H nC ₄ H ₉ OCHFCF ₃ F H n = C ₅ H ₁₁ OCHFCF ₃ F H nc ₆ H ₁₃ OCHFCF ₃ F H H OCHFCF ₃ F F CH ₃ OCHFCF ₃ F F C ₂ H ₅ OCHFCF ₃ F F nC ₃ H ₇ OCHFCF ₃ F F nC ₄ H ₉ OCHFCF ₃ F F nc ₅ H ₁₁ OCHFCF ₃ F F nc ₆ H ₁₃ OCHFCF ₃ F F H OCF ₂ CHFCF ₃ H H CH ₃ OCF ₂ CHFCF ₃ H H C ₂ H ₅ OCF ₂ CHFCF ₃ H H nC ₃ H ₇ OCF ₂ CHFCF ₃ H H nC ₄ H ₉ OCF ₂ CHFCF ₃ H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H H OCF ₂ CHFCF ₃ F H CH ₃ OCF ₂ CHFCF ₃ F H C ₂ H ₅ OCF ₂ CHFCF ₃ F H nC ₃ H ₇ OCF ₂ CHFCF ₃ F H nC ₄ H ₉ OCF ₂ CHFCF ₃ F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H H OCF ₂ CHFCF ₃ F F CH ₃ OCF ₂ CHFCF ₃ F F C ₂ H ₅ OCF ₂ CHFCF ₃ F F nC ₃ H ₇ OCF ₂ CHFCF ₃ F F nC ₄ H ₉ OCF ₂ CHFCF ₃ F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F H NCS H H CH ₃ NCS H H C ₂ H ₅ NCS H H nC ₃ H ₇ NCS H H nC ₄ H ₉ NCS H H nc ₅ H ₁₁ NCS H H nc ₆ H ₁₃ NCS H H H NCS F H CH ₃ NCS F H C ₂ H ₅ NCS F H nC ₃ H ₇ NCS F H nC ₄ H ₉ NCS F H nc ₅ H ₁₁ NCS F H nc ₆ H ₁₃ NCS F H H NCS F F CH ₃ NCS F F C ₂ H ₅ NCS F F nC ₃ H ₇ NCS F F nC ₄ H ₉ NCS F F nc ₅ H ₁₁ NCS F F nc ₆ H ₁₃ NCS F F H C ₂ F ₅ H H CH ₃ C ₂ F ₅ H H C ₂ H ₅ C ₂ F ₅ H H nC ₃ H ₇ C ₂ F ₅ H H nC ₄ H ₉ C ₂ F ₅ H H nc ₅ H ₁₁ C ₂ F ₅ H H nc ₆ H ₁₃ C ₂ F ₅ H H H C ₂ F ₅ F H CH ₃ C ₂ F ₅ F H C ₂ H ₅ C ₂ F ₅ F H nC ₃ H ₇ C ₂ F ₅ F H nC ₄ H ₉ C ₂ F ₅ F H nc ₅ H ₁₁ C ₂ F ₅ F H nc ₆ H ₁₃ C ₂ F ₅ F H H C ₂ F ₅ F F CH ₃ C ₂ F ₅ F F C ₂ H ₅ C ₂ F ₅ F F nC ₃ H ₇ C ₂ F ₅ F F nC ₄ H ₉ C ₂ F ₅ F F nc ₅ H ₁₁ C ₂ F ₅ F F nc ₆ H ₁₃ C ₂ F ₅ F F H C ₃ F ₇ H H CH ₃ C ₃ F ₇ H H C ₂ H ₅ C ₃ F ₇ H H nC ₃ H ₇ C ₃ F ₇ H H nC ₄ H ₉ C ₃ F ₇ H H nc ₅ H ₁₁ C ₃ F ₇ H H nc ₆ H ₁₃ C ₃ F ₇ H H H C ₃ F ₇ F H CH ₃ C ₃ F ₇ F H C ₂ H ₅ C ₃ F ₇ F H _n-C3H7 C ₃ F ₇ F H nC ₄ H ₉ C ₃ F ₇ F H nc ₅ H ₁₁ C ₃ F ₇ F H nc ₆ H ₁₃ C ₃ F ₇ F H H C ₃ F ₇ F F CH ₃ C ₃ F ₇ F F C ₂ H ₅ C ₃ F ₇ F F nC ₃ H ₇ C ₃ F ₇ F F nC ₄ H ₉ C ₃ F ₇ F F nc ₅ H ₁₁ C ₃ F ₇ F F nc ₆ H ₁₃ C ₃ F ₇ F F H SF ₅ H H CH ₃ SF ₅ H H C ₂ H ₅ SF ₅ H H nC ₃ H ₇ SF ₅ H H nC ₄ H ₉ SF ₅ H H nc ₅ H ₁₁ SF ₅ H H nc ₆ H ₁₃ SF ₅ H H H SF ₅ F H CH ₃ SF ₅ F H C ₂ H ₅ SF ₅ F H nC ₃ H ₇ SF ₅ F H nC ₄ H ₉ SF ₅ F H nc ₅ H ₁₁ SF ₅ F H nc ₆ H ₁₃ SF ₅ F H H SF ₅ F F CH ₃ SF ₅ F F C ₂ H ₅ SF ₅ F F nC ₃ H ₇ SF ₅ F F nC ₄ H ₉ SF ₅ F F nc ₅ H ₁₁ SF ₅ F F nc ₆ H ₁₃ SF ₅ F F H CN H H CH ₃ CN H H C ₂ H ₅ CN H H nC ₃ H ₇ CN H H nC ₄ H ₉ CN H H nc ₅ H ₁₁ CN H H nc ₆ H ₁₃ CN H H H CN F H CH ₃ CN F H C ₂ H ₅ CN F H nC ₃ H ₇ CN F H nC ₄ H ₉ CN F H

Example 4

Step 4.1

A solution of 61.2 mmol N in 500 ml of CH ₂ Cl ₂ is added dropwise at -20 ° C with 62.7 mmol of trifluoromethanesulfonic acid. It is allowed to come to room temperature for 30 minutes and then cooled to -70 ° C. Now, a solution of 91 mmol of 4-bromo-phenol and 101 mmol of triethylamine in 200 ml of CH ₂ Cl ₂ , 5 min later added 310 mmol of triethylamine-tris (hydrofluoride). After a further 5 minutes, a suspension of 315 mmol of 1,3-dibromo-5,5-dimethylhydanthoin is added in small portions and the mixture is stirred at -70 ° C. for a further 1 h. It is allowed to come to -10 ° C and the reaction mixture is poured into ice-cold NaOH. The reaction is carried out as usual in water and the crude product is purified by chromatography on silica gel (heptane / MTB ether 4: 1) and crystallization from ethanol at -20 ° C.

Step 4.2

A mixture of 50 mmol of O , 50 mmol of 3,4,5-trifluorobenzeneboronic acid, 2.5 mmol of Pd (PPh ₃ ) ₄ , 300 ml of toluene and 300 ml of Na borate buffer (pH = 9) is stirred at 80 ° C. for 18 h , The mixture is poured into 500 ml of 0.1 N HCl, the product is extracted with CH ₂ Cl ₂ , dried over Na ₂ SO ₄ and rotated to dryness. The crude product is chromatographed on silica gel in n-heptane and then recrystallized from n-heptane at -20 ° C. K 60 S _B 81 N 206.6 I; Δn = 0.1291; Δε = 15.7

hergestellt: R¹ X L¹ L² H F H H CH₃ F H H C₂H₅ F H H n-C₃H₇ F H H n-C₄H₉ F H H n-C₅H₁₁ F H H n-C₆H₁₃ F H H H F F H CH₃ F F H C₂H₅ F F H n-C₃H₇ F F H K 47 S_B 91 N 238,0 I; Δε = 10,7; Δn = 0,1370 n-C₄H₉ F F H n-C₅H₁₁ F F H n-C₆H₁₃ F F H H F F F CH₃ F F F C₂H₅ F F F n-C₄H₉ F F F n-C₅H₁₁ F F F n-C₆H₁₃ F F F H Cl H H CH₃ Cl H H C₂H₅ Cl H H n-C₃H₇ Cl H H n-C₄H₉ Cl H H n-C₅H₁₁ Cl H H n-C₆H₁₃ Cl H H H Cl F H CH₃ Cl F H C₂H₅ Cl F H n-C₃H₇ Cl F H n-C₄H₉ Cl F H n-C₅H₁₁ Cl F H n-C₆H₁₃ Cl F H H Cl F F CH₃ Cl F F C₂H₅ Cl F F n-C₃H₇ Cl F F n-C₄H₉ Cl F F n-C₅H₁₁ Cl F F n-C₆H₁₃ Cl F F H OCF₃ H H CH₃ OCF₃ H H C₂H₅ OCF₃ H H n-C₃H₇ OCF₃ H H n-C₄H₉ OCF₃ H H n-C₅H₁₁ OCF₃ H H n-C₆H₁₃ OCF₃ H H H OCF₃. F H CH₃ OCF₃ F H C₂H₅ OCF₃ F H n-C₃H₇ OCF₃ F H n-C₄H₉ OCF₃ F H n-C₅H₁₁ OCF₃ F H n-C₆H₁₃ OCF₃ F H H OCF₃ F F CH₃ OCF₃ F F C₂H₅ OCF₃ F F n-C₃H₇ OCF₃ F F n-C₄H₉ OCF₃ F F n-C₅H₁₁ OCF₃ F F n-C₆H₁₃ OCF₃ F F H OCHF₂ H H CH₃ OCHF₂ H H C₂H₅ OCHF₂ H H n-C₃H₇ OCHF₂ H H n-C₄H₉ OCHF₂ H H n-C_SH₁₁ OCHF₂ H H n-C₆H₁₃ OCHF₂ H H H OCHF₂ F H CH₃ OCHF₂ F H C₂H₅ OCHF₂ F H n-C₃H₇ OCHF₂ F H n-C₄H₉ OCHF₂ F H n-C₅H₁₁ OCHF₂ F H n-C₆H₁₃ OCHF₂ F H H OCHF₂ F F CH₃ OCHF₂ F F C₂H₅ OCHF₂ F F n-C₃H₇ OCHF₂ F F n-C₄H₉ OCHF₂ F F n-C₅H₁₁ OCHF₂ F F n-C₆H₁₃ OCHF₂ F F H OCHFCF₃ H H CH₃ OCHFCF₃ H H C₂H₅ OCHFCF₃ H H n-C₃H₇ OCHFCF₃ H H n-C₄H₉ OCHFCF₃ H H n-C₅H₁₁ OCHFCF₃ H H n-C₆H₁₃ OCHFCF₃ H H H OCHFCF₃ F H CH₃ OCHFCF₃ F H C₂H₅ OCHFCF₃ F H n-C₃H₇ OCHFCF₃ F H n-C₄H₉ OCHFCF₃ F H n-C₅H₁₁ OCHFCF₃ F H n-C₆H₁₃ OCHFCF₃ F H H OCHFCF₃ F F CH₃ OCHFCF₃ F F C₂H₅ OCHFCF₃ F F n-C₃H₇ OCHFCF₃ F F n-C₄H₉ OCHFCF₃ F F n-C₅H₁₁ OCHFCF₃ F F n-C₆H₁₃ OCHFCF₃ F F H OCHFCF₃ H H CH₃ OCHFCF₃ H H C₂H₅ OCHFCF₃ H H n-C₃H₇ OCHFCF₃ H H n-C₄H₉ OCHFCF₃ H H n-C₅H₁₁ OCHFCF₃ H H n-C₆H₁₃ OCHFCF₃ H H H OCHFCF₃ F H CH₃ OCHFCF₃ F H C₂H₅ OCHFCF₃ F H n-C₃H₇ OCHFCF₃ F H n-C₄H₉ OCHFCF₃ F H n-C₅H₁₁ OCHFCF₃ F H n-C₆H₁₃ OCHFCF₃ F H H OCHFCF₃ F F CH₃ OCHFCF₃ F F C₂H₅ OCHFCF₃ F F n-C₅H₇ OCHFCF₃ F F n-C₄H₉ OCHFCF₃ F F n-C₅H₁₁ OCHFCF₃ F F n-C₆H₁₃ OCHFCF₃ F F H OCF₂CHFCF₃ H H CH₃ OCF₂CHFCF₃ H H C₂H₅ OCF₂CHFCF₃ H H n-C₃H₇ OCF₂CHFCF₃ H H n-C₄H₉ OCF₂CHFCF₃ H H n-C₅H₁₁ OCF₂CHFCF₃ H H n-C₆H₁₃ OCF₂CHFCF₃ H H H OCF₂CHFCF₃ F H CH₃ OCF₂CHFCF₃ F H C₂H₅ OCF₂CHFCF₃ F H n-C₃H₇ OCF₂CHFCF₃ F H n-C₄H₉ OCF₂CHFCF₃ F H n-C₅H₁₁ OCF₂CHFCF₃ F H n-C₆H₁₃ OCF₂CHFCF₃ F H H OCF₂CHFCF₃ F F CH₃ OCF₂CHFCF₃ F F C₂H₅ OCF₂CHFCF₃ F F n-C₃H₇ OCF₂CHFCF₃ F F n-C₄H₉ OCF₂CHFCF₃ F F n-C₅H₁₁ OCF₂CHFCF₃ F F n-C₆H₁₃ OCF₂CHFCF₃ F F H NCS H H CH₃ NCS H H C₂H₅ NCS H H n-C₃H₇ NCS H H n-C₄H₉ NCS H H n-C₅H₁₁ NCS H H n-C₆H₁₃ NCS H H H NCS F H CH₃ NCS F H C₂H₅ NCS F H n-C₃H₇ NCS F H n-C₄H₉ NCS F H n-C₅H₁₁ NCS F H n-C₆H₁₃ NCS F H H NCS F F CH₃ NCS F F C₂H₅ NCS F F n-C₃H₇ NCS F F n-C₄H₉ NCS F F n-C₅H₁₁ NCS . F F n-C₆H₁₃ NCS F F H C₂F₅ H H CH₃ C₂F₅ H H C₂H₅ C₂F₅ H H n-C₃H₇ C₂F₅ H H n-C₄H₉ C₂F₅ H H n-C₅H₁₁ C₂F₅ H H n-C₆H₁₃ C₂F₅ H H H C₂F₅ F H CH₃ C₂F₅ F H C₂H₅ C₂F₅ F H n-C₃H₇ C₂F₅ F H n-C₄H₉ C₂F₅ F H n-C₅H₁₁ C₂F₅ F H n-C₆H₁₃ C₂F₅ F H H C₂F₅ F F CH₃ C₂F₅ F F C₂H₅ C₂F₅ F F n-C₃H₇ C₂F₅ F F n-C₄H₉ C₂F₅ F F n-C₅H₁₁ C₂F₅ F F n-C₆H₁₃ C₂F₅ F F H C₃F₇ H H CH₃ C₃F₇ H H C₂H₅ C₃F₇ H H n-C₃H₇ C₃F₇ H H n-C₄H₉ C₃F₇ H H n-C₅H₁₁ C₃F₇ H H n-C₆H₁₃ C₃F₇ H H H C₃F₇ F H CH₃ C₃F₇ F H C₂H₅ C₃F₇ F H n-C₃H₇ C₃F₇ F H n-C₄H₉ C₃F₇ F H n-C₅H₁₁ C₃F₇ F H n-C₆H₁₃ C₃F₇ F H H C₃F₇ F F CH₃ C₃F₇ F F C₂H₅ C₃F₇ F F n-C₃H₇ C₃F₇ F F n-C₄H₉ C₃F₇ F F n-C₅H₁₁ C₃F₇ F F n-C₆H₁₃ C₃F₇ F F H SF₅ H H CH₃ SF₅ H H C₂H₅ SF₅ H H n-C₃H₇ SF₅ H H n-C₄H₉ SF₅ H H n-C₅H₁₁ SF₅ H H n-C₆H₁₃ SF₅ H H H SF₅ F H CH₃ SF₅ F H C₂H₅ SF₅ F H n-C₃H₇ SF₅ F H n-C₄H₉ SF₅ F H n-C₅H₁₁ SF₅ F H n-C₆H₁₃ SF₅ F H H SF₅ F F CH₃ SF₅ F F C₂H₅ SF₅ F F n-C₃H₇ SF₅ F F n-C₄H₉ SF₅ F F n-C₅H₁₁ SF₅ F F n-C₆H₁₃ SF₅ F F H CN H H CH₃ CN H H C₂H₅ CN H H n-C₃H₇ CN H H n-C₄H₉ CN H H n-C₅H₁₁ CN H H n-C₆H₁₃ CN H H Analogously, the following compounds of the formula

produced: R ¹ X L ¹ L ² H F H H CH ₃ F H H C ₂ H ₅ F H H nC ₃ H ₇ F H H nC ₄ H ₉ F H H nc ₅ H ₁₁ F H H nc ₆ H ₁₃ F H H H F F H CH ₃ F F H C ₂ H ₅ F F H nC ₃ H ₇ F F H K 47 S _B 91 N 238.0 I; Δε = 10.7; Δn = 0.1370 nC ₄ H ₉ F F H nc ₅ H ₁₁ F F H nc ₆ H ₁₃ F F H H F F F CH ₃ F F F C ₂ H ₅ F F F nC ₄ H ₉ F F F nc ₅ H ₁₁ F F F nc ₆ H ₁₃ F F F H Cl H H CH ₃ Cl H H C ₂ H ₅ Cl H H nC ₃ H ₇ Cl H H nC ₄ H ₉ Cl H H nc ₅ H ₁₁ Cl H H nc ₆ H ₁₃ Cl H H H Cl F H CH ₃ Cl F H C ₂ H ₅ Cl F H nC ₃ H ₇ Cl F H nC ₄ H ₉ Cl F H nc ₅ H ₁₁ Cl F H nc ₆ H ₁₃ Cl F H H Cl F F CH ₃ Cl F F C ₂ H ₅ Cl F F nC ₃ H ₇ Cl F F nC ₄ H ₉ Cl F F nc ₅ H ₁₁ Cl F F nc ₆ H ₁₃ Cl F F H OCF ₃ H H CH ₃ OCF ₃ H H C ₂ H ₅ OCF ₃ H H nC ₃ H ₇ OCF ₃ H H nC ₄ H ₉ OCF ₃ H H nc ₅ H ₁₁ OCF ₃ H H nc ₆ H ₁₃ OCF ₃ H H H OCF ₃ . F H CH ₃ OCF ₃ F H C ₂ H ₅ OCF ₃ F H nC ₃ H ₇ OCF ₃ F H nC ₄ H ₉ OCF ₃ F H nc ₅ H ₁₁ OCF ₃ F H nc ₆ H ₁₃ OCF ₃ F H H OCF ₃ F F CH ₃ OCF ₃ F F C ₂ H ₅ OCF ₃ F F nC ₃ H ₇ OCF ₃ F F nC ₄ H ₉ OCF ₃ F F nc ₅ H ₁₁ OCF ₃ F F nc ₆ H ₁₃ OCF ₃ F F H OCHF ₂ H H CH ₃ OCHF ₂ H H C ₂ H ₅ OCHF ₂ H H nC ₃ H ₇ OCHF ₂ H H nC ₄ H ₉ OCHF ₂ H H nC _S H ₁₁ OCHF ₂ H H nc ₆ H ₁₃ OCHF ₂ H H H OCHF ₂ F H CH ₃ OCHF ₂ F H C ₂ H ₅ OCHF ₂ F H nC ₃ H ₇ OCHF ₂ F H nC ₄ H ₉ OCHF ₂ F H nc ₅ H ₁₁ OCHF ₂ F H nc ₆ H ₁₃ OCHF ₂ F H H OCHF ₂ F F CH ₃ OCHF ₂ F F C ₂ H ₅ OCHF ₂ F F nC ₃ H ₇ OCHF ₂ F F nC ₄ H ₉ OCHF ₂ F F nc ₅ H ₁₁ OCHF ₂ F F nc ₆ H ₁₃ OCHF ₂ F F H OCHFCF ₃ H H CH ₃ OCHFCF ₃ H H C ₂ H ₅ OCHFCF ₃ H H nC ₃ H ₇ OCHFCF ₃ H H nC ₄ H ₉ OCHFCF ₃ H H nc ₅ H ₁₁ OCHFCF ₃ H H nc ₆ H ₁₃ OCHFCF ₃ H H H OCHFCF ₃ F H CH ₃ OCHFCF ₃ F H C ₂ H ₅ OCHFCF ₃ F H nC ₃ H ₇ OCHFCF ₃ F H nC ₄ H ₉ OCHFCF ₃ F H nc ₅ H ₁₁ OCHFCF ₃ F H nc ₆ H ₁₃ OCHFCF ₃ F H H OCHFCF ₃ F F CH ₃ OCHFCF ₃ F F C ₂ H ₅ OCHFCF ₃ F F nC ₃ H ₇ OCHFCF ₃ F F nC ₄ H ₉ OCHFCF ₃ F F nc ₅ H ₁₁ OCHFCF ₃ F F nc ₆ H ₁₃ OCHFCF ₃ F F H OCHFCF ₃ H H CH ₃ OCHFCF ₃ H H C ₂ H ₅ OCHFCF ₃ H H nC ₃ H ₇ OCHFCF ₃ H H nC ₄ H ₉ OCHFCF ₃ H H nc ₅ H ₁₁ OCHFCF ₃ H H nc ₆ H ₁₃ OCHFCF ₃ H H H OCHFCF ₃ F H CH ₃ OCHFCF ₃ F H C ₂ H ₅ OCHFCF ₃ F H nC ₃ H ₇ OCHFCF ₃ F H nC ₄ H ₉ OCHFCF ₃ F H nc ₅ H ₁₁ OCHFCF ₃ F H nc ₆ H ₁₃ OCHFCF ₃ F H H OCHFCF ₃ F F CH ₃ OCHFCF ₃ F F C ₂ H ₅ OCHFCF ₃ F F nc ₅ H ₇ OCHFCF ₃ F F nC ₄ H ₉ OCHFCF ₃ F F nc ₅ H ₁₁ OCHFCF ₃ F F nc ₆ H ₁₃ OCHFCF ₃ F F H OCF ₂ CHFCF ₃ H H CH ₃ OCF ₂ CHFCF ₃ H H C ₂ H ₅ OCF ₂ CHFCF ₃ H H nC ₃ H ₇ OCF ₂ CHFCF ₃ H H nC ₄ H ₉ OCF ₂ CHFCF ₃ H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H H OCF ₂ CHFCF ₃ F H CH ₃ OCF ₂ CHFCF ₃ F H C ₂ H ₅ OCF ₂ CHFCF ₃ F H nC ₃ H ₇ OCF ₂ CHFCF ₃ F H nC ₄ H ₉ OCF ₂ CHFCF ₃ F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H H OCF ₂ CHFCF ₃ F F CH ₃ OCF ₂ CHFCF ₃ F F C ₂ H ₅ OCF ₂ CHFCF ₃ F F nC ₃ H ₇ OCF ₂ CHFCF ₃ F F nC ₄ H ₉ OCF ₂ CHFCF ₃ F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F H NCS H H CH ₃ NCS H H C ₂ H ₅ NCS H H nC ₃ H ₇ NCS H H nC ₄ H ₉ NCS H H nc ₅ H ₁₁ NCS H H nc ₆ H ₁₃ NCS H H H NCS F H CH ₃ NCS F H C ₂ H ₅ NCS F H nC ₃ H ₇ NCS F H nC ₄ H ₉ NCS F H nc ₅ H ₁₁ NCS F H nc ₆ H ₁₃ NCS F H H NCS F F CH ₃ NCS F F C ₂ H ₅ NCS F F nC ₃ H ₇ NCS F F nC ₄ H ₉ NCS F F nc ₅ H ₁₁ NCS. F F nc ₆ H ₁₃ NCS F F H C ₂ F ₅ H H CH ₃ C ₂ F ₅ H H C ₂ H ₅ C ₂ F ₅ H H nC ₃ H ₇ C ₂ F ₅ H H nC ₄ H ₉ C ₂ F ₅ H H nc ₅ H ₁₁ C ₂ F ₅ H H nc ₆ H ₁₃ C ₂ F ₅ H H H C ₂ F ₅ F H CH ₃ C ₂ F ₅ F H C ₂ H ₅ C ₂ F ₅ F H nC ₃ H ₇ C ₂ F ₅ F H nC ₄ H ₉ C ₂ F ₅ F H nc ₅ H ₁₁ C ₂ F ₅ F H nc ₆ H ₁₃ C ₂ F ₅ F H H C ₂ F ₅ F F CH ₃ C ₂ F ₅ F F C ₂ H ₅ C ₂ F ₅ F F nC ₃ H ₇ C ₂ F ₅ F F nC ₄ H ₉ C ₂ F ₅ F F nc ₅ H ₁₁ C ₂ F ₅ F F nc ₆ H ₁₃ C ₂ F ₅ F F H C ₃ F ₇ H H CH ₃ C ₃ F ₇ H H C ₂ H ₅ C ₃ F ₇ H H nC ₃ H ₇ C ₃ F ₇ H H nC ₄ H ₉ C ₃ F ₇ H H nc ₅ H ₁₁ C ₃ F ₇ H H nc ₆ H ₁₃ C ₃ F ₇ H H H C ₃ F ₇ F H CH ₃ C ₃ F ₇ F H C ₂ H ₅ C ₃ F ₇ F H nC ₃ H ₇ C ₃ F ₇ F H nC ₄ H ₉ C ₃ F ₇ F H nc ₅ H ₁₁ C ₃ F ₇ F H nc ₆ H ₁₃ C ₃ F ₇ F H H C ₃ F ₇ F F CH ₃ C ₃ F ₇ F F C ₂ H ₅ C ₃ F ₇ F F nC ₃ H ₇ C ₃ F ₇ F F nC ₄ H ₉ C ₃ F ₇ F F nc ₅ H ₁₁ C ₃ F ₇ F F nc ₆ H ₁₃ C ₃ F ₇ F F H SF ₅ H H CH ₃ SF ₅ H H C ₂ H ₅ SF ₅ H H nC ₃ H ₇ SF ₅ H H nC ₄ H ₉ SF ₅ H H nc ₅ H ₁₁ SF ₅ H H nc ₆ H ₁₃ SF ₅ H H H SF ₅ F H CH ₃ SF ₅ F H C ₂ H ₅ SF ₅ F H nC ₃ H ₇ SF ₅ F H nC ₄ H ₉ SF ₅ F H nc ₅ H ₁₁ SF ₅ F H nc ₆ H ₁₃ SF ₅ F H H SF ₅ F F CH ₃ SF ₅ F F C ₂ H ₅ SF ₅ F F nC ₃ H ₇ SF ₅ F F nC ₄ H ₉ SF ₅ F F nc ₅ H ₁₁ SF ₅ F F nc ₆ H ₁₃ SF ₅ F F H CN H H CH ₃ CN H H C ₂ H ₅ CN H H nC ₃ H ₇ CN H H nC ₄ H ₉ CN H H nc ₅ H ₁₁ CN H H nc ₆ H ₁₃ CN H H

Example 5

Step 5.1 1

To a cooled to -70 ° C solution of 65 mmol P in 100 ml of dichloromethane, a mixture of 98 mmol of Q and 16.3 ml of triethylamine (117 mmol) in 80 ml of dichloromethane is added dropwise with stirring. After complete addition, the mixture is stirred at -70 ° C for a further 1 h. Subsequently, 325 mmol Triethylamintrishydrofluorid added dropwise at the same temperature. Subsequently, 325 mmol of bromine are added dropwise at -70 ° C. After 1 h stirring at -70 ° C is allowed to warm to -10 ° C and the reaction mixture is poured into a mixture of 500 ml of ice water and 95 ml of 32% sodium hydroxide solution. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are worked up as usual.

Step 5.2

A mixture of 10 mmol S and 10 mmol of 2,6-difluoro-4- (trans-5'-propyltetrahydropyranyl (2)) -phenylboronic acid in 60 ml of toluene and 60 ml of sodium borate buffer solution (pH = 9) is assigned 0, 5 mmol of Pd (PPh ₃ ) ₄ with stirring for 16 h at 80 ° C heated. After cooling, the biphasic reaction mixture is poured with stirring onto 100 ml of 0.1 N HCl, the organic phase separated and the aqueous phase extracted twice with toluene. The combined toluene phases are evaporated after drying and the residue is filtered through silica gel (heptane / methyl tert-butyl ether). Finally, it is first recrystallized from ethanol and then from n-heptane.
K 115 N 197.7 I; Δ∈ = 35.4; An = 0.1706

hergestellt. R¹ X L¹ L² L³ L⁴ H F H H H H CH₃ F H H H H C₂H₅ F H H H H C₃H₇ F H H H H n-C₄H₉ F H H H H n-C₅H₁₁ F H H H H n-C₆H₁₃ F H H H H H F F H H H CH₃ F F H H H C₂H₅ F F H H H n-C₃H₇ F F H H H n-C₄H₉ F F H H H n-C₅H₁₁ F F H H H n-C₆H₁₃ F F H H H H F F F H H CH₃ F F F H H n-C₄H₉ F F F H H n-C₅H₁₁ F F F H H n-C₆H₁₃ F F F H H H Cl H H H H CH₃ Cl H H H H C₂H₅ Cl H H H H n-C₃H₇ Cl H H H H n-C₄H₉ Cl H H H H n-C₅H₁₁ Cl H H H H n-C₆H₁₃ Cl H H H H H Cl F H H H CH₃ Cl F H H H C₂H₅ Cl F H H H n-C₃H₇ Cl F H H H n-C₄H₉ Cl F H H H n-C₅H₁₁ Cl F H H H n-C₆H₁₃ Cl F H H H H Cl F F H H CH₃ Cl F F H H C₂H₅ Cl F F H H n-C₃H₇ Cl F F H H n-C₄H₉ Cl F F H H n-C₅H₁₁ Cl F F H H n-C₆H₁₃ Cl F F H H H OCF₃ H H H H CH₃ OCF₃ H H H H C₂H₅ OCF₃ H H H H n-C₃H₇ OCF₃ H H H H n-C₄H₉ OCF₃ H H H H n-C₅H₁₁ OCF₃ H H H H n-C₆H₁₃ OCF₃ H H H H H OCF₃ F H H H CH₃ OCF₃ F H H H C₂H₅ OCF₃ F H H H n-C₃H₇ OCF₃ F H H H n-C₄H₉ OCF₃ F H H H n-C₅H₁₁ OCF₃ F H H H n-C₆H₁₃ OCF₃ F H H H H OCF₃ F F H H CH₃ OCF₃ F F H H C₂H₅ OCF₃ F F H H n-C₃H₇ OCF₃ F F H H n-C₄H₉ OCF₃ F F H H n-C₅H₁₁ OCF₃ F F H H n-C₆H₁₃ OCF₃ F F H H H OCHF₂ H H H H CH₃ OCHF₂ H H H H C₂H₅ OCHF₂ H H H H n-C₃H₇ OCHF₂ H H H H n-C₄H₉ OCHF₂ H H H H n-C₅H₁₁ OCHF₂ H H H H n-C₆H₁₃ OCHF₂ H H H H H OCHF₂ F H H H CH₃ OCHF₂ F H H H C₂H₅ OCHF₂ F H H H n-C₃H₇ OCHF₂ F H H H n-C₄H₉ OCHF₂ F H H H n-C₅H₁₁ OCHF₂ F H H H n-C₆H₁₃ OCHF₂ F H H H H OCHF₂ F F H H CH₃ OCHF₂ F F H H C₂H₅ OCHF₂ F F H H n-C₃H₇ OCHF₂ F F H H n-C₄H₉ OCHF₂ F F H H n-C₅H₁₁ OCHF₂ F F H H n-C₆H₁₃ OCHF₂ F F H H H OCHFCF₃ H H H H CH₃ OCHFCF₃ H H H H C₂H₅ OCHFCF₃ H H H H n-C₃H₇ OCHFCF₃ H H H H n-C₄H₉ OCHFCF₃ H H H H n-C₅H₁₁ OCHFCF₃ H H H H n-C₆H₁₃ OCHFCF₃ H H H H H OCHFCF₃ F H H H CH₃ OCHFCF₃ F H H H C₂H₅ OCHFCF₃ F H H H n-C₃H₇ OCHFCF₃ F H H H n-C₄H₉ OCHFCF₃ F H H H n-C₅H₁₁ OCHFCF₃ F H H H n-C₆H₁₃ OCHFCF₃ F H H H H OCHFCF₃ F F H H CH₃ OCHFCF₃ F F H H C₂H₅ OCHFCF₃ F F H H n-C₃H₇ OCHFCF₃ F F H H n-C₄H₉ OCHFCF₃ F F H H n-C₅H₁₁ OCHFCF₃ F F H H n-C₆H₁₃ OCHFCF₃ F F H H H OCHFCF₃ H H H H CH₃ OCHFCF₃ H H H H C₂H₅ OCHFCF₃ H H H H n-C₃H₇ OCHFCF₃ H H H H n-C₄H₉ OCHFCF₃ H H H H n-C₅H₁₁ OCHFCF₃ H H H H n-C₆H₁₃ OCHFCF₃ H H H H H OCHFCF₃ F H H H CH₃ OCHFCF₃ F H H H C₂H₅ OCHFCF₃ F H H H n-C₃H₇ OCHFCF₃ F H H H n-C₄Hg. OCHFCF₃ F H H H n-C₅H₁₁ OCHFCF₃ F H H H n-C₆H₁₃ OCHFCF₃ F H H H H OCHFCF₃ F F H H CH₃ OCHFCF₃ F F H H C₂H₅ OCHFCF₃ F F H H n-C₃H₇ OCHFCF₃ F F H H n-C₄H₉ OCHFCF₃ F F H H n-C₅H₁₁ OCHFCF₃ F F H H n-C₆H₁₃ OCHFCF₃ F F H H H OCF₂CHFCF₃ H H H H CH₃ OCF₂CHFCF₃ H H H H C₂H₅ OCF₂CHFCF₃ H H H H n-C₃H₇ OCF₂CHFCF₃ H H H H n-C₄H₉ OCF₂CHFCF₃ H H H H n-C₅H₁₁ OCF₂CHFCF₃ H H H H n-C₆H₁₃ OCF₂CHFCF₃ H H H H H OCF₂CHFCF₃ F H H H CH₃ OCF₂CHFCF₃ F H H H C₂H₅ OCF₂CHFCF₃ F H H H n-C₃H₇ OCF₂CHFCF₃ F H H H n-C₄H₉ OCF₂CHFCF₃ F H H H n-C₅H₁₁ OCF₂CHFCF₃ F H H H n-C₆H₁₃ OCF₂CHFCF₃ F H H H H OCF₂CHFCF₃ F F H H CH₃ OCF₂CHFCF₃ F F H H C₂H₅ OCF₂CHFCF₃ F F H H n-C₃H₇ OCF₂CHFCF₃ F F H H n-C₄H₉ OCF₂CHFCF₃ F F H H n-C₅H₁₁ OCF₂CHFCF₃ F F H H n-C₆H₁₃ OCF₂CHFCF₃ F F H H H NCS H H H H CH₃ NCS H H H H C₂H₅ NCS H H H H n-C₃H₇ NCS H H H H n-C₄H₉ NCS H H H H n-C₅H₁₁ NCS H H H H n-C₆H₁₃ NCS H H H H H NCS F H H H CH₃ NCS F H H H C₂H₅ NCS F H H H n-C₃H₇ NCS F H H H n-C₄H₉ NCS F H H H n-C₅H₁₁ NCS F H H H n-C₆H₁₃ NCS F H H H H NCS F F H H CH₃ NCS F F H H C₂H₅ NCS F F H H n-C₃H₇ NCS F F H H n-C₄H₉ NCS F F H H n-C₅H₁₁ NCS F F H H n-C₆H₁₃ NCS F F H H H C₂F₅ H H H H CH₃ C₂F₅ H H H H C₂H₅ C₂F₅ H H H H n-C₃H₇ C₂F₅ H H H H n-C₄H₉ C₂F₅ H H H H n-C₅H₁₁ C₂F₅ H H H H n-C₆H₁₃ C₂F₅ H H H H H C₂F₅ F H H H CH₃ C₂F₅ F H H H C₂H₅ C₂F₅ F H H H n-C₃H₇ C₂F₅ F H H H n-C₄H₉ C₂F₅ F H H H n-C₅H₁₁ C₂F₅ F H H H n-C₆H₁₃ C₂F₅ F H H H H C₂F₅ F F H H CH₃ C₂F₅ F F H H C₂H₅ C₂F₅ F F H H n-C₃H₇ C₂F₅ F F H H n-C₄H₉ C₂F₅ F F H H n-C₅H₁₁ C₂F₅ F F H H n-C₆H₁₃ C₂F₅ F F H H H C₃F₇ H H H H CH₃ C₃F₇ H H H H C₂H₅ C₃F₇ H H H H n-C₃H₇ C₃F₇ H H H H n-C₄H₉ C₃F₇ H H H H n-C₅H₁₁ C₃F₇ H H H H n-C₆H₁₃ C₃F₇ H H H H H C₃F₇ F H H H CH₃ C₃F₇ F H H H C₂H₅ C₃F₇ F H H H n-C₃H₇ C₃F₇ F H H H n-C₄H₉ C₃F₇ F H H H n-C₅H₁₁ C₃F₇ F H H H n-C₆H₁₃ C₃F₇ F H H H H C₃F₇ F F H H CH₃ C₃F₇ F F H H C₂H₅ C₃F₇ F F H H n-C₃H₇ C₃F₇ F F H H n-C₄H₉ C₃F₇ F F H H n-C₅H₁₁ C₃F₇ F F H H n-C₆H₁₃ C₃F₇ F F H H H SF₅ H H H H CH₃ SF₅ H H H H C₂H₅ SF₅ H H H H n-C₃H₇ SF₅ H H H H n-C₄H₉ SF₅ H H H H n-C₅H₁₁ SF₅ H H H H n-C₆H₁₃ SF₅ H H H H H SF₅ F H H H CH₃ SF₅ F H H H C₂H₅ SF₅ F H H H n-C₃H₇ SF₅ F H H H n-C₄H₉ SF₅ F H H H n-C₅H₁₁ SF₅ F H H H n-C₆H₁₃ SF₅ F H H H H SF₅ F F H H CH₃ SF₅ F F H H C₂H₅ SF₅ F F H H n-C₃H₇ SF₅ F F H H n-C₄H₉ SF₅ F F H H n-C₅H₁₁ SF₅ F F H H n-C₆H₁₃ SF₅ F F H H H CN H H H H CH₃ CN H H H H C₂H₅ CN H H H H n-C₃H₇ CN H H H H n-C₄H₉ CN H H H H n-C₅H₁₁ CN H H H H n-C₆H₁₃ CN H H H H H CN F H H H CH₃ CN F H H H C₂H₅ CN F H H H n-C₃H₇ CN F H H H n-C₄H₉ CN F H H H n-C₅H₁₁ CN F H H H n-C₆H₁₃ CN F H H H H CN F F H H CH₃ CN F F H H C₂H₅ CN F F H H n-C₃H₇ CN F F H H n-C₄H₉ CN F F H H n-C₅H₁₁ CN F F H H n-C₆H₁₃ CN F F H H H F H H F H CH₃ F H H F H C₂H₅ F H H F H C₃H₇ F H H F H n-C₄H₉ F H H F H n-C₅H₁₁ F H H F H n-C₆H₁₃ F H H F H H F F H F H CH₃ F F H F H C₂H₅ F F H F H n-C₃H₇ F F H F H n-C₄H₉ F F H F H n-C₅H₁₁ F F H F H n-C₆H₁₃ F F H F H H F F F F H CH₃ F F F F H C₂H₅ F F F F H n-C₃H₇ F F F F H K 98 N 193,0 I, Δε = 37,9; Δn = 0,1649 n-C₄H₉ F F F F H n-C₅H₁₁ F F F F H n-C₆H₁₃ F F F F H H Cl H H F H CH₃ Cl H H F H C₂H₅ Cl H H F H n-C₃H₇ Cl H H F H n-C₄H₉ Cl H H F H n-C₅H₁₁ Cl H H F H n-C₆H₁₃ Cl H H F H H Cl F H F H CH₃ Cl F H F H C₂H₅ Cl F H F H n-C₃H₇ Cl F H F H n-C₄H₉ Cl F H F H n-C₅H₁₁ Cl F H F H n-C₆H₁₃ Cl F H F H H Cl F F F H CH₃ Cl F F F H C₂H₅ Cl F F F H n-C₃H₇ Cl F F F H n-C₄H₉ Cl F F F H n-C₅H₁₁ Cl F F F H n-C₆H₁₃ Cl F F F H H OCF₃ H H F H CH₃ OCF₃ H H F H C₂H₅ OCF₃ H H F H n-C₃H₇ OCF₃ H H F H n-C₄H₉ OCF₃ H H F H n-C₅H₁₁ OCF₃ H H F H n-C₆H₁₃ OCF₃ H H F H H OCF₃ F H F H CH₃ OCF₃ F H F H C₂H₅ OCF₃ F H F H n-C₃H₇ OCF₃ F H F H n-C₄H₉ OCF₃ F H F H n-C₅H₁₁ OCF₃ F H F H n-C₆H₁₃ OCF₃ F H F H H OCF₃ F F F H CH₃ OCF₃ F F F H C₂H₅ OCF₃ F F F H n-C₃H₇ OCF₃ F F F H n-C₄H₉ OCF₃ F F F H n-C₅H₁₁ OCF₃ F F F H n-C₆H₁₃ OCF₃ F F F H H OCHF₂ H H F H CH₃ OCHF₂ H H F H C₂H₅ OCHF₂ H H F H n-C₃H₇ OCHF₂ H H F H n-C₄H₉ OCHF₂ H H F H n-C₅H₁₁ OCHF₂ H H F H n-C₆H₁₃ OCHF₂ H H F H H OCHF₂ F H F H CH₃ OCHF₂ F H F H C₂H₅ OCHF₂ F H F H n-C₃H₇ OCHF₂ F H F H n-C₄H₉ OCHF₂ F H F H n-C₅H₁₁ OCHF₂ F H F H n-C₆H₁₃ OCHF₂ F H F H H OCHF₂ F F F H CH₃ OCHF₂ F F F H C₂H₅ OCHF₂ F F F H n-C₃H₇ OCHF₂ F F F H n-C₄H₉ OCHF₂ F F F H n-C₅H₁₁ OCHF₂ F F F H n-C₆H₁₃ OCHF₂ F F F H H OCHFCF₃ H H F H CH₃ OCHFCF₃ H H F H C₂H₅ OCHFCF₃ H H F H n-C₃H₇ OCHFCF₃ H H F H n-C₄H₉ OCHFCF₃ H H F H n-C₅H₁₁ OCHFCF₃ H H F H n-C₆H₁₃ OCHFCF₃ H H F H H OCHFCF₃ F H F H CH₃ OCHFCF₃ F H F H C₂H₅ OCHFCF₃ F H F H n-C₃H₇ OCHFCF₃ F H F H n-C₄H₉ OCHFCF₃ F H F H n-C₅H₁₁ OCHFCF₃ F H F H n-C₆H₁₃ OCHFCF₃ F H F H H OCHFCF₃ F F F H CH₃ OCHFCF₃ F F F H C₂H₅ OCHFCF₃ F F F H n-C₃H₇ OCHFCF₃ F F F H n-C₄H₉ OCHFCF₃ F F F H n-C₅H₁₁ OCHFCF₃ F F F H n-C₆H₁₃ OCHFCF₃ F F F H H OCHFCF₃ H H F H CH₃ OCHFCF₃ H H F H C₂H₅ OCHFCF₃ H H F H n-C₃H₇ OCHFCF₃ H H F H n-C₄H₉ OCHFCF₃ H H F H n-C₅H₁₁ OCHFCF₃ H H F H n-C₆H₁₃ OCHFCF₃ H H F H H OCHFCF₃ F H F H CH₃ OCHFCF₃ F H F H C₂H₅ OCHFCF₃ F H F H n-C₃H₇ OCHFCF₃ F H F H n-C₄H₉ OCHFCF₃ F H F H n-C₅H₁₁ OCHFCF₃ F H F H n-C₆H₁₃ OCHFCF₃ F H F H H OCHFCF₃ F F F H CH₃ OCHFCF₃ F F F H C₂H₅ OCHFCF₃ F F F H n-C₃H₇ OCHFCF₃ F F F H n-C₄H₉ OCHFCF₃ F F F H n-C₅H₁₁ OCHFCF₃ F F F H n-C₆H₁₃ OCHFCF₃ F F F H H OCF₂CHFCF₃ H H F H CH₃ OCF₂CHFCF₃ H H F H C₂H₅ OCF₂CHFCF₃ H H F H n-C₃H₇ OCF₂CHFCF₃ H H F H n-C₄H₉ OCF₂CHFCF₃ H H F H n-C₅H₁₁ OCF₂CHFCF₃ H H F H n-C₆H₁₃ OCF₂CHFCF₃ H H F H H OCF₂CHFCF₃ F H F H CH₃ OCF₂CHFCF₃ F H F H C₂H₅ OCF₂CHFCF₃ F H F H n-C₃H₇ OCF₂CHFCF₃ F H F H n-C₄H₉ OCF₂CHFCF₃ F H F H n-C₅H₁₁ OCF₂CHFCF₃ F H F H n-C₆H₁₃ OCF₂CHFCF₃ F H F H H OCF₂CHFCF₃ F F F H CH₃ OCF₂CHFCF₃ F F F H C₂H₅ OCF₂CHFCF₃ F F F H n-C₃H₇ OCF₂CHFCF₃ F F F H n-C₄H₉ OCF₂CHFCF₃ F F F H n-C₅H₁₁ OCF₂CHFCF₃ F F F H n-C₆H₁₃ OCF₂CHFCF₃ F F F H H NCS H H F H CH₃ NCS H H F H C₂H₅ NCS H H F H n-C₃H₇ NCS H H F H n-C₄H₉ NCS H H F H n-C₅H₁₁ NCS H H F H n-C₆H₁₃ NCS H H F H H NCS F H F H CH₃ NCS F H F H C₂H₅ NCS F H F H n-C₃H₇ NCS F H F H n-C₄H₉ NCS F H F H n-C₅H₁₁ NCS F H F H n-C₆H₁₃ NCS F H F H H NCS F F F H CH₃ NCS F F F H C₂H₅ NCS F F F H n-C₃H₇ NCS F F F H n-C₄H₉ NCS F F F H n-C₅H₁₁ NCS F F F H n-C₆H₁₃ NCS F F F H H C₂F₅ H H F H CH₃ C₂F₅ H H F H C₂H₅ C₂F₅ H H F H n-C₃H₇ C₂F₅ H H F H n-C₄H₉ C₂F₅ H H F H n-C₅H₁₁ C₂F₅ H H F H n-C₆H₁₃ C₂F₅ H H F H H C₂F₅ F H F H CH₃ C₂F₅ F H F H C₂H₅ C₂F₅ F H F H n-C₃H₇ C₂F₅ F H F H n-C₄H₉ C₂F₅ F H F H n-C₅H₁₁ C₂F₅ F H F H n-C₆H₁₃ C₂F₅ F H F H H C₂F₅ F F F H CH₃ C₂F₅ F F F H C₂H₅ C₂F₅ F F F H n-C₃H₇ C₂F₅ F F F H n-C₄H₉ C₂F₅ F F F H n-C₅H₁₁ C₂F₅ F F F H n-C₆H,₃ C₂F₅ F F F H H C₃F₇ H H F H CH₃ C₃F₇ H H F H C₂H₅ C₃F₇ H H F H n-C₃H₇ C₃F₇ H H F H n-C₄H₉ C₃F₇ H H F H n-C₅H₁₁ C₃F₇ H H F H n-C₆H₁₃ C₃F₇ H H F H H C₃F₇ F H F H CH₃ C₃F₇ F H F H C₂H₅ C₃F₇ F H F H n-C₃H₇ C₃F₇ F H F H n-C₄H₉ C₃F₇ F H F H n-C₅H₁₁ C₃F₇ F H F H n-C₆H₁₃ C₃F₇ F H F H H C₃F₇ F F F H CH₃ C₃F₇ F F F H C₂H₅ C₃F₇ F F F H n-C₃H₇ C₃F₇ F F F H n-C₄H₉ C₃F₇ F F F H n-C₅H₁₁ C₃F₇ F F F H n-C₆H₁₃ C₃H₇ F F F H H SF₅ H H F H CH₃ SF₅ H H F H C₂H₅ SF₅ H H F H n-C₃H₇ SF₅ H H F H n-C₄H₉ SF₅ H H F H n-C₅H₁₁ SF₅ H H F H n-C₆H₁₃ SF₅ H H F H H SF₅ F H F H CH₃ SF₅ F H F H C₂H₅ SF₅ F H F H n-C₃H₇ SF₅ F H F H n-C₄H₉ SF₅ F H F H n-C₅H₁₁ SF₅ F H F H n-C₆H₁₃ SF₅ F H F H H SF₅ F F F H CH₃ SF₅ F F F H C₂H₅ SF₅ F F F H n-C₃H₇ SF₅ F F F H n-C₄H₉ SF₅ F F F H n-C₅H₁₁ SF₅ F F F H n-C₆H₁₃ SF₅ F F F H H CN H H F H CH₃ CN H H F H C₂H₅ CN H H F H n-C₃H₇ CN H H F H n-C₄H₉ CN H H F H n-C₅H₁₁ CN H H F H n-C₆H₁₃ CN H H F H H CN F H F H CH₃ CN F H F H C₂H₅ CN F H F H n-C₃H₇ CN F H F H n-C₄H₉ CN F H F H n-C₅H₁₁ CN F H F H n-C₆H₁₃ CN F H F H H CN F F F H CH₃ CN F F F H C₂H₅ CN F F F H n-C₃H₇ CN F F F H n-C₄H₉ CN F F F H n-C₅H₁₁ CN F F F H n-C₆H₁₃ CN F F F H H F H H F F CH₃ F H H F F C₂H₅ F H H F F n-C₄H₉ F H H F F n-C₅H₁₁ F H H F F n-C₆H₁₃ F H H F F H F F H F F CH₃ F F H F F C₂H₅ F F H F F n-C₃H₇ F F H F F n-C₄H₉ F F H F F n-C₅H₁₁ F F H F F n-C₆H₁₃ F F H F F H F F F F F CH₃ F F F F F C₂H₅ F F F F F C₂H₅ F F F F F n-C₃H₇ F F F F F K 144 N 181,4 I; Δε = 42,1; Δn = 0,1510 n-C₄H₉ F F F F F n-C₅H₁₁ F F F F F n-C₆H₁₃ F F F F F H Cl H H F F CH₃ Cl H H F F C₂H₅ Cl H H F F n-C₃H₇ Cl H H F F n-C₄H₉ Cl H H F F n-C₅H₁₁ Cl H H F F n-C₆H₁₃ Cl H H F F H Cl F H F F CH₃ Cl F H F F C₂H₅ Cl F H F F n-C₃H₇ Cl F H F F n-C₄H₉ Cl F H F F n-C₅H₁₁ Cl F H F F n-C₆H₁₃ Cl F H F F H Cl F F F F CH₃ Cl F F F F C₂H₅ Cl F F F F n-C₃H₇ Cl F F F F n-C₄H₉ Cl F F F F n-C₅H₁₁ Cl F F F F n-C₆H₁₃ Cl F F F F H OCF₃ H H F F CH₃ OCF₃ H H F F C₂H₅ OCF₃ H H F F n-C₃H₇ OCF₃ H H F F n-C₄H₉ OCF₃ H H F -F n-C₅H₁₁ OCF₃ H H F F n-C₆H₁₃ OCF₃ H H F F H OCF₃ F H F F CH₃ OCF₃ F H F F C₂H₅ OCF₃ F H F F n-C₃H₇ OCF₃ F H F F K 121 N 205,2 I; Δε = 37,7; Δn = 0,1634 n-C₄H₉ OCF₃ F H F F n-C₅H₁₁ OCF₃ F H F F n-C₆H₁₃ OCF₃ F H F F H OCF₃ F F F F CH₃ OCF₃ F F F F C₂H₅ OCF₃ F F F F n-C₃H₇ OCF₃ F F F F K 128 N 201,2 I; Δε = 43,8; Δn = 0,1411 n-C₄H₉ OCF₃ F F F F n-C₅H₁₁ OCF₃ F F F F n-C₆H₁₃ OCF₃ F F F F H OCHF₂ H H F F CH₃ OCHF₂ H H F F C₂H₅ OCHF₂ H H F F n-C₃H₇ OCHF₂ H H F F n-C₄H₉ OCHF₂ H H F F n-C₅H₁₁ OCHF₂ H H F F n-C₆H₁₃ OCHF₂ H H F F H OCHF₂ F H F F CH₃ OCHF₂ F H F F C₂H₅ OCHF₂ F H F F n-C₃H₇ OCHF₂ F H F F n-C₄H₉ OCHF₂ F H F F n-C₅H₁₁ OCHF₂ F H F F n-C₆H₁₃ OCHF₂ F H F F H OCHF₂ F F F F CH₃ OCHF₂ F F F F C₂H₅ OCHF₂ F F F F n-C₃H₇ OCHF₂ F F F F n-C₄H₉ OCHF₂ F F F F n-C₅H₁₁ OCHF₂ F F F F n-C₆H₁₃ OCHF₂ F F F F H OCHFCF₃ H H F F CH₃ OCHFCF₃ H H F F C₂H₅ OCHFCF₃ H H F F n-C₃H₇ OCHFCF₃ H H F F n-C₄H₉ OCHFCF₃ H H F F n-C₅H₁₁ OCHFCF₃ H H F F n-C₆H₁₃ OCHFCF₃ H H F F H OCHFCF₃ F H F F CH₃ OCHFCF₃ F H F F C₂H₅ OCHFCF₃ F H F F n-C₃H₇ OCHFCF₃ F H F F n-C₄H₉ OCHFCF₃ F H F F n-C₅H₁₁ OCHFCF₃ F H F F n-C₆H₁₃ OCHFCF₃ F H F F H OCHFCF₃ F F F F CH₃ OCHFCF₃ F F F F C₂H₅ OCHFCF₃ F F F F n-C₃H₇ OCHFCF₃ F F F F n-C₄H₉ OCHFCF₃ F F F F n-C₅H₁₁ OCHFCF₃ F F F F n-C₆H₁₃ OCHFCF₃ F F F F H OCHFCF₃ H H F F CH₃ OCHFCF₃ H H F F C₂H₅ OCHFCF₃ H H F F n-C₃H₇ OCHFCF₃ H H F F n-C₄H₉ OCHFCF₃ H H F F n-C₅H₁₁ OCHFCF₃ H H F F n-C₆H₁₃ OCHFCF₃ H H F F H OCHFCF₃ F H F F CH₃ OCHFCF₃ F H F F C₂H₅ OCHFCF₃ F H F F n-C₃H₇ OCHFCF₃ F H F F n-C₄H₉ OCHFCF₃ F H F F n-C₅H₁₁ OCHFCF₃ F H F F n-C₆H₁₃ OCHFCF₃ F H F F H OCHFCF₃ F F F F CH₃ OCHFCF₃ F F F F C₂H₅ OCHFCF₃ F F F F n-C₃H₇ OCHFCF₃ F F F F n-C₄H₉ OCHFCF₃ F F F F n-C₅H₁₁ OCHFCF₃ F F F F n-C₆H₁₃ OCHFCF₃ F F F F H OCF₂CHFCF₃ H H F F CH₃ OCF₂CHFCF₃ H H F F C₂H₅ OCF₂CHFCF₃ H H F F n-C₃H₇ OCF₂CHFCF₃ H H F F n-C₄H₉ OCF₂CHFCF₃ H H F F n-C₅H₁₁ OCF₂CHFCF₃ H H F F n-C₆H₁₃ OCF₂CHFCF₃ H H F F H OCF₂CHFCF₃ F H F F CH₃ OCF₂CHFCF₃ F H F F C₂H₅ OCF₂CHFCF₃ F H F F n-C₃H₇ OCF₂CHFCF₃ F H F F n-C₄H₉ OCF₂CHFCF₃ F H F F n-C₅H₁₁ OCF₂CHFCF₃ F H F F n-C₆H₁₃ OCF₂CHFCF₃ F H F F H OCF₂CHFCF₃ F F F F CH₃ OCF₂CHFCF₃ F F F F C₂H₅ OCF₂CHFCF₃ F F F F n-C₃H₇ OCF₂CHFCF₃ F F F F n-C₄H₉ OCF₂CHFCF₃ F F F F n-C₅H₁₁ OCF₂CHFCF₃ F F F F n-C₆H₁₃ OCF₂CHFCF₃ F F F F H NCS H H F F CH₃ NCS H H F F C₂H₅ NCS H H F F n-C₃H₇ NCS H H F F n-C₄H₉ NCS H H F F n-C₅H₁₁ NCS H H F F n-C₆H₁₃ NCS H H F F H NCS F H F F CH₃ NCS F H F F C₂H₅ NCS F H F F n-C₃H₇ NCS F H F F n-C₄H₉ NCS F H F F n-C₅H₁₁ NCS F H F F n-C₆H₁₃ NCS F H F F H NCS F F F F CH₃ NCS F F F F C₂H₅ NCS F F F F n-C₃H₇ NCS F F F F n-C₄H₉ NCS F F F F n-C₅H₁₁ NCS F F F F n-C₆H₁₃ NCS F F F F H C₂F₅ H H F F CH₃ C₂F₅ H H F F C₂H₅ C₂F₅ H H F F n-C₃H₇ C₂F₅ H H F F n-C₄H₉ C₂F₅ H H F F n-C₅H₁₁ C₂F₅ H H F F n-C₆H₁₃ C₂F₅ H H F F H C₂F₅ F H F F CH₃ C₂F_s F H F F C₂H₅ C₂F₅ F H F F n-C₃H₇ C₂F₅ F H F F n-C₄H₉ C₂F₅ F H F F n-C₅H₁₁ C₂F₅ F H F F n-C₆H₁₃ C₂F₅ F H F F H C₂F₅ F F F F CH₃ C₂F₅ F F F F C₂H₅ C₂F₅ F F F F n-C₃H₇ C₂F₅ F F F F n-C₄H₉ C₂F₅ F F F F n-C₅H₁₁ C₂F₅ F F F F n-C₆H₁₃ C₂F₅ F F F F H C₃F₇ H H F F CH₃ C₃F₇ H H F F C₂H₅ C₃F₇ H H F F n-C₃H₇ C₃F₇ H H F F n-C₄H₉ C₃F₇ H H F F n-C₅H₁₁ C₃F₇ H H F F n-C₅H₁₃ C₃F₇ H H F F H C₃F₇ F H F F CH₃ C₃F₇ F H F F C₂H₅ C₃F₇ F H F F n-C₃H₇ C₃F₇ F H F F n-C₄H₉ C₃F₇ F H F F n-C₅H₁₁ C₃F₇ F H F F n-C₆H₁₃ C₃F₇ F H F F H C₃F₇ F F F F CH₃ C₃F₇ F F F F C₂H₅ C₃F₇ F F F F n-C₃H₇ C₃F₇ F F F F n-C₄H₉ C₃F₇ F F F F n-C₅H₁₁ C₃F₇ F F F F n-C₆H₁₃ C₃F₇ F F F F H SF₅ H H F F CH₃ SF₅ H H F F C₂H₅ SF₅ H H F F n-C₃H₇ SF₅ H H F F n-C₄H₉ SF₅ H H F F n-C₅H₁₁ SF₅ H H F F n-C₆H₁₃ SF₅ H H F F H SF₅ F H F F CH₃ SF₅ F H F F C₂H₅ SF₅ F H F F n-C₃H₇ SF₅ F H F F n-C₄H₉ SF₅ F H F F n-C₅H₁₁ SF₅ F H F F n-C₆H₁₃ SF₅ F H F F H SF₅ F F F F CH₃ SF₅ F F F F C₂H₅ SF₅ F F F F n-C₃H₇ SF₅ F F F F n-C₄H₉ SF₅ F F F F n-C₅H₁₁ SF₅ F F F F n-C₆H₁₃ SF₅ F F F F H CN H H F F CH₃ CN H H F F C₂H₅ CN H H F F n-C₃H₇ CN H H F F n-C₄H₉ CN H H F F n-C₅H₁₁ CN H H F F n-C₆H₁₃ CN H H F F H CN F H F F CH₃ CN F H F F C₂H₅ CN F H F F n-C₃H₇ CN F H F F n-C₄H₉ CN F H F F n-C₅H₁₁ CN F H F F n-C₆H₁₃ CN F H F F H CN F F F F CH₃ CN F F F F C₂H₅ CN F F F F n-C₃H₇ CN F F F F n-C₄H₉ CN F F F F n-C₅H₁₁ CN F F F F n-C₆H₁₃ CN F F F F H CF₃ H H F F C₂H₅ CF₃ H H F F n-C₃H₇ CF₃ H H F F n-C₄H₉ CF₃ H H F F n-C₅H₁₁ CF₃ H H F F n-C₆H₁₃ CF₃ H H F F CH₂=CH CF₃ H H F F H CF₃ F F F F C₂H₅ CF₃ F F F F n-C₃H₇ CF₃ F F F F n-C₄H₉ CF₃ F F F F n-C₅H₁₁ CF₃ F F F F n-C₆H₁₃ CF₃ F F F F CH₂=CH CF₃ F F F F H F H H F F C₂H₅ F H H F F n-C₃H₇ F H H F F n-C₄H₉ F H H F F n-C₅H₁₁ F H H F F n-C₆H₁₃ F H H F F CH₂=CH F H H F F Analogously, the following compounds of the formula

produced. R ¹ X L ¹ L ² L ³ L ⁴ H F H H H H CH ₃ F H H H H C ₂ H ₅ F H H H H C ₃ H ₇ F H H H H nC ₄ H ₉ F H H H H nc ₅ H ₁₁ F H H H H nc ₆ H ₁₃ F H H H H H F F H H H CH ₃ F F H H H C ₂ H ₅ F F H H H nC ₃ H ₇ F F H H H nC ₄ H ₉ F F H H H nc ₅ H ₁₁ F F H H H nc ₆ H ₁₃ F F H H H H F F F H H CH ₃ F F F H H nC ₄ H ₉ F F F H H nc ₅ H ₁₁ F F F H H nc ₆ H ₁₃ F F F H H H Cl H H H H CH ₃ Cl H H H H C ₂ H ₅ Cl H H H H nC ₃ H ₇ Cl H H H H nC ₄ H ₉ Cl H H H H nc ₅ H ₁₁ Cl H H H H nc ₆ H ₁₃ Cl H H H H H Cl F H H H CH ₃ Cl F H H H C ₂ H ₅ Cl F H H H nC ₃ H ₇ Cl F H H H nC ₄ H ₉ Cl F H H H nc ₅ H ₁₁ Cl F H H H nc ₆ H ₁₃ Cl F H H H H Cl F F H H CH ₃ Cl F F H H C ₂ H ₅ Cl F F H H nC ₃ H ₇ Cl F F H H nC ₄ H ₉ Cl F F H H nc ₅ H ₁₁ Cl F F H H nc ₆ H ₁₃ Cl F F H H H OCF ₃ H H H H CH ₃ OCF ₃ H H H H C ₂ H ₅ OCF ₃ H H H H nC ₃ H ₇ OCF ₃ H H H H nC ₄ H ₉ OCF ₃ H H H H nc ₅ H ₁₁ OCF ₃ H H H H nc ₆ H ₁₃ OCF ₃ H H H H H OCF ₃ F H H H CH ₃ OCF ₃ F H H H C ₂ H ₅ OCF ₃ F H H H nC ₃ H ₇ OCF ₃ F H H H nC ₄ H ₉ OCF ₃ F H H H nc ₅ H ₁₁ OCF ₃ F H H H nc ₆ H ₁₃ OCF ₃ F H H H H OCF ₃ F F H H CH ₃ OCF ₃ F F H H C ₂ H ₅ OCF ₃ F F H H nC ₃ H ₇ OCF ₃ F F H H nC ₄ H ₉ OCF ₃ F F H H nc ₅ H ₁₁ OCF ₃ F F H H nc ₆ H ₁₃ OCF ₃ F F H H H OCHF ₂ H H H H CH ₃ OCHF ₂ H H H H C ₂ H ₅ OCHF ₂ H H H H nC ₃ H ₇ OCHF ₂ H H H H nC ₄ H ₉ OCHF ₂ H H H H nc ₅ H ₁₁ OCHF ₂ H H H H nc ₆ H ₁₃ OCHF ₂ H H H H H OCHF ₂ F H H H CH ₃ OCHF ₂ F H H H C ₂ H ₅ OCHF ₂ F H H H nC ₃ H ₇ OCHF ₂ F H H H nC ₄ H ₉ OCHF ₂ F H H H nc ₅ H ₁₁ OCHF ₂ F H H H nc ₆ H ₁₃ OCHF ₂ F H H H H OCHF ₂ F F H H CH ₃ OCHF ₂ F F H H C ₂ H ₅ OCHF ₂ F F H H nC ₃ H ₇ OCHF ₂ F F H H nC ₄ H ₉ OCHF ₂ F F H H nc ₅ H ₁₁ OCHF ₂ F F H H nc ₆ H ₁₃ OCHF ₂ F F H H H OCHFCF ₃ H H H H CH ₃ OCHFCF ₃ H H H H C ₂ H ₅ OCHFCF ₃ H H H H nC ₃ H ₇ OCHFCF ₃ H H H H nC ₄ H ₉ OCHFCF ₃ H H H H nc ₅ H ₁₁ OCHFCF ₃ H H H H nc ₆ H ₁₃ OCHFCF ₃ H H H H H OCHFCF ₃ F H H H CH ₃ OCHFCF ₃ F H H H C ₂ H ₅ OCHFCF ₃ F H H H nC ₃ H ₇ OCHFCF ₃ F H H H nC ₄ H ₉ OCHFCF ₃ F H H H nc ₅ H ₁₁ OCHFCF ₃ F H H H nc ₆ H ₁₃ OCHFCF ₃ F H H H H OCHFCF ₃ F F H H CH ₃ OCHFCF ₃ F F H H C ₂ H ₅ OCHFCF ₃ F F H H nC ₃ H ₇ OCHFCF ₃ F F H H nC ₄ H ₉ OCHFCF ₃ F F H H nc ₅ H ₁₁ OCHFCF ₃ F F H H nc ₆ H ₁₃ OCHFCF ₃ F F H H H OCHFCF ₃ H H H H CH ₃ OCHFCF ₃ H H H H C ₂ H ₅ OCHFCF ₃ H H H H nC ₃ H ₇ OCHFCF ₃ H H H H nC ₄ H ₉ OCHFCF ₃ H H H H nc ₅ H ₁₁ OCHFCF ₃ H H H H nc ₆ H ₁₃ OCHFCF ₃ H H H H H OCHFCF ₃ F H H H CH ₃ OCHFCF ₃ F H H H C ₂ H ₅ OCHFCF ₃ F H H H nC ₃ H ₇ OCHFCF ₃ F H H H nc ₄ Hg. OCHFCF ₃ F H H H nc ₅ H ₁₁ OCHFCF ₃ F H H H nc ₆ H ₁₃ OCHFCF ₃ F H H H H OCHFCF ₃ F F H H CH ₃ OCHFCF ₃ F F H H C ₂ H ₅ OCHFCF ₃ F F H H nC ₃ H ₇ OCHFCF ₃ F F H H nC ₄ H ₉ OCHFCF ₃ F F H H nc ₅ H ₁₁ OCHFCF ₃ F F H H nc ₆ H ₁₃ OCHFCF ₃ F F H H H OCF ₂ CHFCF ₃ H H H H CH ₃ OCF ₂ CHFCF ₃ H H H H C ₂ H ₅ OCF ₂ CHFCF ₃ H H H H nC ₃ H ₇ OCF ₂ CHFCF ₃ H H H H nC ₄ H ₉ OCF ₂ CHFCF ₃ H H H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H H H H OCF ₂ CHFCF ₃ F H H H CH ₃ OCF ₂ CHFCF ₃ F H H H C ₂ H ₅ OCF ₂ CHFCF ₃ F H H H nC ₃ H ₇ OCF ₂ CHFCF ₃ F H H H nC ₄ H ₉ OCF ₂ CHFCF ₃ F H H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H H H H OCF ₂ CHFCF ₃ F F H H CH ₃ OCF ₂ CHFCF ₃ F F H H C ₂ H ₅ OCF ₂ CHFCF ₃ F F H H nC ₃ H ₇ OCF ₂ CHFCF ₃ F F H H nC ₄ H ₉ OCF ₂ CHFCF ₃ F F H H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F H H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F H H H NCS H H H H CH ₃ NCS H H H H C ₂ H ₅ NCS H H H H nC ₃ H ₇ NCS H H H H nC ₄ H ₉ NCS H H H H nc ₅ H ₁₁ NCS H H H H nc ₆ H ₁₃ NCS H H H H H NCS F H H H CH ₃ NCS F H H H C ₂ H ₅ NCS F H H H nC ₃ H ₇ NCS F H H H nC ₄ H ₉ NCS F H H H nc ₅ H ₁₁ NCS F H H H nc ₆ H ₁₃ NCS F H H H H NCS F F H H CH ₃ NCS F F H H C ₂ H ₅ NCS F F H H nC ₃ H ₇ NCS F F H H nC ₄ H ₉ NCS F F H H nc ₅ H ₁₁ NCS F F H H nc ₆ H ₁₃ NCS F F H H H C ₂ F ₅ H H H H CH ₃ C ₂ F ₅ H H H H C ₂ H ₅ C ₂ F ₅ H H H H nC ₃ H ₇ C ₂ F ₅ H H H H nC ₄ H ₉ C ₂ F ₅ H H H H nc ₅ H ₁₁ C ₂ F ₅ H H H H nc ₆ H ₁₃ C ₂ F ₅ H H H H H C ₂ F ₅ F H H H CH ₃ C ₂ F ₅ F H H H C ₂ H ₅ C ₂ F ₅ F H H H nC ₃ H ₇ C ₂ F ₅ F H H H nC ₄ H ₉ C ₂ F ₅ F H H H nc ₅ H ₁₁ C ₂ F ₅ F H H H nc ₆ H ₁₃ C ₂ F ₅ F H H H H C ₂ F ₅ F F H H CH ₃ C ₂ F ₅ F F H H C ₂ H ₅ C ₂ F ₅ F F H H nC ₃ H ₇ C ₂ F ₅ F F H H nC ₄ H ₉ C ₂ F ₅ F F H H nc ₅ H ₁₁ C ₂ F ₅ F F H H nc ₆ H ₁₃ C ₂ F ₅ F F H H H C ₃ F ₇ H H H H CH ₃ C ₃ F ₇ H H H H C ₂ H ₅ C ₃ F ₇ H H H H nC ₃ H ₇ C ₃ F ₇ H H H H nC ₄ H ₉ C ₃ F ₇ H H H H nc ₅ H ₁₁ C ₃ F ₇ H H H H nc ₆ H ₁₃ C ₃ F ₇ H H H H H C ₃ F ₇ F H H H CH ₃ C ₃ F ₇ F H H H C ₂ H ₅ C ₃ F ₇ F H H H nC ₃ H ₇ C ₃ F ₇ F H H H nC ₄ H ₉ C ₃ F ₇ F H H H nc ₅ H ₁₁ C ₃ F ₇ F H H H nc ₆ H ₁₃ C ₃ F ₇ F H H H H C ₃ F ₇ F F H H CH ₃ C ₃ F ₇ F F H H C ₂ H ₅ C ₃ F ₇ F F H H nC ₃ H ₇ C ₃ F ₇ F F H H nC ₄ H ₉ C ₃ F ₇ F F H H nc ₅ H ₁₁ C ₃ F ₇ F F H H nc ₆ H ₁₃ C ₃ F ₇ F F H H H SF ₅ H H H H CH ₃ SF ₅ H H H H C ₂ H ₅ SF ₅ H H H H nC ₃ H ₇ SF ₅ H H H H nC ₄ H ₉ SF ₅ H H H H nc ₅ H ₁₁ SF ₅ H H H H nc ₆ H ₁₃ SF ₅ H H H H H SF ₅ F H H H CH ₃ SF ₅ F H H H C ₂ H ₅ SF ₅ F H H H nC ₃ H ₇ SF ₅ F H H H nC ₄ H ₉ SF ₅ F H H H nc ₅ H ₁₁ SF ₅ F H H H nc ₆ H ₁₃ SF ₅ F H H H H SF ₅ F F H H CH ₃ SF ₅ F F H H C ₂ H ₅ SF ₅ F F H H nC ₃ H ₇ SF ₅ F F H H nC ₄ H ₉ SF ₅ F F H H nc ₅ H ₁₁ SF ₅ F F H H nc ₆ H ₁₃ SF ₅ F F H H H CN H H H H CH ₃ CN H H H H C ₂ H ₅ CN H H H H nC ₃ H ₇ CN H H H H nC ₄ H ₉ CN H H H H nc ₅ H ₁₁ CN H H H H nc ₆ H ₁₃ CN H H H H H CN F H H H CH ₃ CN F H H H C ₂ H ₅ CN F H H H nC ₃ H ₇ CN F H H H nC ₄ H ₉ CN F H H H nc ₅ H ₁₁ CN F H H H nc ₆ H ₁₃ CN F H H H H CN F F H H CH ₃ CN F F H H C ₂ H ₅ CN F F H H nC ₃ H ₇ CN F F H H nC ₄ H ₉ CN F F H H nc ₅ H ₁₁ CN F F H H nc ₆ H ₁₃ CN F F H H H F H H F H CH ₃ F H H F H C ₂ H ₅ F H H F H C ₃ H ₇ F H H F H nC ₄ H ₉ F H H F H nc ₅ H ₁₁ F H H F H nc ₆ H ₁₃ F H H F H H F F H F H CH ₃ F F H F H C ₂ H ₅ F F H F H nC ₃ H ₇ F F H F H nC ₄ H ₉ F F H F H nc ₅ H ₁₁ F F H F H nc ₆ H ₁₃ F F H F H H F F F F H CH ₃ F F F F H C ₂ H ₅ F F F F H nC ₃ H ₇ F F F F H K 98 N 193.0 I, Δε = 37.9; Δn = 0.1649 nC ₄ H ₉ F F F F H nc ₅ H ₁₁ F F F F H nc ₆ H ₁₃ F F F F H H Cl H H F H CH ₃ Cl H H F H C ₂ H ₅ Cl H H F H nC ₃ H ₇ Cl H H F H nC ₄ H ₉ Cl H H F H nc ₅ H ₁₁ Cl H H F H nc ₆ H ₁₃ Cl H H F H H Cl F H F H CH ₃ Cl F H F H C ₂ H ₅ Cl F H F H nC ₃ H ₇ Cl F H F H nC ₄ H ₉ Cl F H F H nc ₅ H ₁₁ Cl F H F H nc ₆ H ₁₃ Cl F H F H H Cl F F F H CH ₃ Cl F F F H C ₂ H ₅ Cl F F F H nC ₃ H ₇ Cl F F F H nC ₄ H ₉ Cl F F F H nc ₅ H ₁₁ Cl F F F H nc ₆ H ₁₃ Cl F F F H H OCF ₃ H H F H CH ₃ OCF ₃ H H F H C ₂ H ₅ OCF ₃ H H F H nC ₃ H ₇ OCF ₃ H H F H nC ₄ H ₉ OCF ₃ H H F H nc ₅ H ₁₁ OCF ₃ H H F H nc ₆ H ₁₃ OCF ₃ H H F H H OCF ₃ F H F H CH ₃ OCF ₃ F H F H C ₂ H ₅ OCF ₃ F H F H nC ₃ H ₇ OCF ₃ F H F H nC ₄ H ₉ OCF ₃ F H F H nc ₅ H ₁₁ OCF ₃ F H F H nc ₆ H ₁₃ OCF ₃ F H F H H OCF ₃ F F F H CH ₃ OCF ₃ F F F H C ₂ H ₅ OCF ₃ F F F H nC ₃ H ₇ OCF ₃ F F F H nC ₄ H ₉ OCF ₃ F F F H nc ₅ H ₁₁ OCF ₃ F F F H nc ₆ H ₁₃ OCF ₃ F F F H H OCHF ₂ H H F H CH ₃ OCHF ₂ H H F H C ₂ H ₅ OCHF ₂ H H F H nC ₃ H ₇ OCHF ₂ H H F H nC ₄ H ₉ OCHF ₂ H H F H nc ₅ H ₁₁ OCHF ₂ H H F H nc ₆ H ₁₃ OCHF ₂ H H F H H OCHF ₂ F H F H CH ₃ OCHF ₂ F H F H C ₂ H ₅ OCHF ₂ F H F H nC ₃ H ₇ OCHF ₂ F H F H nC ₄ H ₉ OCHF ₂ F H F H nc ₅ H ₁₁ OCHF ₂ F H F H nc ₆ H ₁₃ OCHF ₂ F H F H H OCHF ₂ F F F H CH ₃ OCHF ₂ F F F H C ₂ H ₅ OCHF ₂ F F F H nC ₃ H ₇ OCHF ₂ F F F H nC ₄ H ₉ OCHF ₂ F F F H nc ₅ H ₁₁ OCHF ₂ F F F H nc ₆ H ₁₃ OCHF ₂ F F F H H OCHFCF ₃ H H F H CH ₃ OCHFCF ₃ H H F H C ₂ H ₅ OCHFCF ₃ H H F H nC ₃ H ₇ OCHFCF ₃ H H F H nC ₄ H ₉ OCHFCF ₃ H H F H nc ₅ H ₁₁ OCHFCF ₃ H H F H nc ₆ H ₁₃ OCHFCF ₃ H H F H H OCHFCF ₃ F H F H CH ₃ OCHFCF ₃ F H F H C ₂ H ₅ OCHFCF ₃ F H F H nC ₃ H ₇ OCHFCF ₃ F H F H nC ₄ H ₉ OCHFCF ₃ F H F H nc ₅ H ₁₁ OCHFCF ₃ F H F H nc ₆ H ₁₃ OCHFCF ₃ F H F H H OCHFCF ₃ F F F H CH ₃ OCHFCF ₃ F F F H C ₂ H ₅ OCHFCF ₃ F F F H nC ₃ H ₇ OCHFCF ₃ F F F H nC ₄ H ₉ OCHFCF ₃ F F F H nc ₅ H ₁₁ OCHFCF ₃ F F F H nc ₆ H ₁₃ OCHFCF ₃ F F F H H OCHFCF ₃ H H F H CH ₃ OCHFCF ₃ H H F H C ₂ H ₅ OCHFCF ₃ H H F H nC ₃ H ₇ OCHFCF ₃ H H F H nC ₄ H ₉ OCHFCF ₃ H H F H nc ₅ H ₁₁ OCHFCF ₃ H H F H nc ₆ H ₁₃ OCHFCF ₃ H H F H H OCHFCF ₃ F H F H CH ₃ OCHFCF ₃ F H F H C ₂ H ₅ OCHFCF ₃ F H F H nC ₃ H ₇ OCHFCF ₃ F H F H nC ₄ H ₉ OCHFCF ₃ F H F H nc ₅ H ₁₁ OCHFCF ₃ F H F H nc ₆ H ₁₃ OCHFCF ₃ F H F H H OCHFCF ₃ F F F H CH ₃ OCHFCF ₃ F F F H C ₂ H ₅ OCHFCF ₃ F F F H nC ₃ H ₇ OCHFCF ₃ F F F H nC ₄ H ₉ OCHFCF ₃ F F F H nc ₅ H ₁₁ OCHFCF ₃ F F F H nc ₆ H ₁₃ OCHFCF ₃ F F F H H OCF ₂ CHFCF ₃ H H F H CH ₃ OCF ₂ CHFCF ₃ H H F H C ₂ H ₅ OCF ₂ CHFCF ₃ H H F H nC ₃ H ₇ OCF ₂ CHFCF ₃ H H F H nC ₄ H ₉ OCF ₂ CHFCF ₃ H H F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H F H H OCF ₂ CHFCF ₃ F H F H CH ₃ OCF ₂ CHFCF ₃ F H F H C ₂ H ₅ OCF ₂ CHFCF ₃ F H F H nC ₃ H ₇ OCF ₂ CHFCF ₃ F H F H nC ₄ H ₉ OCF ₂ CHFCF ₃ F H F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H F H H OCF ₂ CHFCF ₃ F F F H CH ₃ OCF ₂ CHFCF ₃ F F F H C ₂ H ₅ OCF ₂ CHFCF ₃ F F F H nC ₃ H ₇ OCF ₂ CHFCF ₃ F F F H nC ₄ H ₉ OCF ₂ CHFCF ₃ F F F H nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F F H nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F F H H NCS H H F H CH ₃ NCS H H F H C ₂ H ₅ NCS H H F H nC ₃ H ₇ NCS H H F H nC ₄ H ₉ NCS H H F H nc ₅ H ₁₁ NCS H H F H nc ₆ H ₁₃ NCS H H F H H NCS F H F H CH ₃ NCS F H F H C ₂ H ₅ NCS F H F H nC ₃ H ₇ NCS F H F H nC ₄ H ₉ NCS F H F H nc ₅ H ₁₁ NCS F H F H nc ₆ H ₁₃ NCS F H F H H NCS F F F H CH ₃ NCS F F F H C ₂ H ₅ NCS F F F H nC ₃ H ₇ NCS F F F H nC ₄ H ₉ NCS F F F H nc ₅ H ₁₁ NCS F F F H nc ₆ H ₁₃ NCS F F F H H C ₂ F ₅ H H F H CH ₃ C ₂ F ₅ H H F H C ₂ H ₅ C ₂ F ₅ H H F H nC ₃ H ₇ C ₂ F ₅ H H F H nC ₄ H ₉ C ₂ F ₅ H H F H nc ₅ H ₁₁ C ₂ F ₅ H H F H nc ₆ H ₁₃ C ₂ F ₅ H H F H H C ₂ F ₅ F H F H CH ₃ C ₂ F ₅ F H F H C ₂ H ₅ C ₂ F ₅ F H F H nC ₃ H ₇ C ₂ F ₅ F H F H nC ₄ H ₉ C ₂ F ₅ F H F H nc ₅ H ₁₁ C ₂ F ₅ F H F H nc ₆ H ₁₃ C ₂ F ₅ F H F H H C ₂ F ₅ F F F H CH ₃ C ₂ F ₅ F F F H C ₂ H ₅ C ₂ F ₅ F F F H nC ₃ H ₇ C ₂ F ₅ F F F H nC ₄ H ₉ C ₂ F ₅ F F F H nc ₅ H ₁₁ C ₂ F ₅ F F F H nC ₆ H, ₃ C ₂ F ₅ F F F H H C ₃ F ₇ H H F H CH ₃ C ₃ F ₇ H H F H C ₂ H ₅ C ₃ F ₇ H H F H nC ₃ H ₇ C ₃ F ₇ H H F H nC ₄ H ₉ C ₃ F ₇ H H F H nc ₅ H ₁₁ C ₃ F ₇ H H F H nc ₆ H ₁₃ C ₃ F ₇ H H F H H C ₃ F ₇ F H F H CH ₃ C ₃ F ₇ F H F H C ₂ H ₅ C ₃ F ₇ F H F H nC ₃ H ₇ C ₃ F ₇ F H F H nC ₄ H ₉ C ₃ F ₇ F H F H nc ₅ H ₁₁ C ₃ F ₇ F H F H nc ₆ H ₁₃ C ₃ F ₇ F H F H H C ₃ F ₇ F F F H CH ₃ C ₃ F ₇ F F F H C ₂ H ₅ C ₃ F ₇ F F F H nC ₃ H ₇ C ₃ F ₇ F F F H nC ₄ H ₉ C ₃ F ₇ F F F H nc ₅ H ₁₁ C ₃ F ₇ F F F H nc ₆ H ₁₃ C ₃ H ₇ F F F H H SF ₅ H H F H CH ₃ SF ₅ H H F H C ₂ H ₅ SF ₅ H H F H nC ₃ H ₇ SF ₅ H H F H nC ₄ H ₉ SF ₅ H H F H nc ₅ H ₁₁ SF ₅ H H F H nc ₆ H ₁₃ SF ₅ H H F H H SF ₅ F H F H CH ₃ SF ₅ F H F H C ₂ H ₅ SF ₅ F H F H nC ₃ H ₇ SF ₅ F H F H nC ₄ H ₉ SF ₅ F H F H nc ₅ H ₁₁ SF ₅ F H F H nc ₆ H ₁₃ SF ₅ F H F H H SF ₅ F F F H CH ₃ SF ₅ F F F H C ₂ H ₅ SF ₅ F F F H nC ₃ H ₇ SF ₅ F F F H nC ₄ H ₉ SF ₅ F F F H nc ₅ H ₁₁ SF ₅ F F F H nc ₆ H ₁₃ SF ₅ F F F H H CN H H F H CH ₃ CN H H F H C ₂ H ₅ CN H H F H nC ₃ H ₇ CN H H F H nC ₄ H ₉ CN H H F H nc ₅ H ₁₁ CN H H F H nc ₆ H ₁₃ CN H H F H H CN F H F H CH ₃ CN F H F H C ₂ H ₅ CN F H F H nC ₃ H ₇ CN F H F H nC ₄ H ₉ CN F H F H nc ₅ H ₁₁ CN F H F H nc ₆ H ₁₃ CN F H F H H CN F F F H CH ₃ CN F F F H C ₂ H ₅ CN F F F H nC ₃ H ₇ CN F F F H nC ₄ H ₉ CN F F F H nc ₅ H ₁₁ CN F F F H nc ₆ H ₁₃ CN F F F H H F H H F F CH ₃ F H H F F C ₂ H ₅ F H H F F nC ₄ H ₉ F H H F F nc ₅ H ₁₁ F H H F F nc ₆ H ₁₃ F H H F F H F F H F F CH ₃ F F H F F C ₂ H ₅ F F H F F nC ₃ H ₇ F F H F F nC ₄ H ₉ F F H F F nc ₅ H ₁₁ F F H F F nc ₆ H ₁₃ F F H F F H F F F F F CH ₃ F F F F F C ₂ H ₅ F F F F F C ₂ H ₅ F F F F F nC ₃ H ₇ F F F F F K 144 N 181.4 I; Δε = 42.1; Δn = 0.1510 nC ₄ H ₉ F F F F F nc ₅ H ₁₁ F F F F F nc ₆ H ₁₃ F F F F F H Cl H H F F CH ₃ Cl H H F F C ₂ H ₅ Cl H H F F nC ₃ H ₇ Cl H H F F nC ₄ H ₉ Cl H H F F nc ₅ H ₁₁ Cl H H F F nc ₆ H ₁₃ Cl H H F F H Cl F H F F CH ₃ Cl F H F F C ₂ H ₅ Cl F H F F nC ₃ H ₇ Cl F H F F nC ₄ H ₉ Cl F H F F nc ₅ H ₁₁ Cl F H F F nc ₆ H ₁₃ Cl F H F F H Cl F F F F CH ₃ Cl F F F F C ₂ H ₅ Cl F F F F nC ₃ H ₇ Cl F F F F nC ₄ H ₉ Cl F F F F nc ₅ H ₁₁ Cl F F F F nc ₆ H ₁₃ Cl F F F F H OCF ₃ H H F F CH ₃ OCF ₃ H H F F C ₂ H ₅ OCF ₃ H H F F nC ₃ H ₇ OCF ₃ H H F F nC ₄ H ₉ OCF ₃ H H F -F nc ₅ H ₁₁ OCF ₃ H H F F nc ₆ H ₁₃ OCF ₃ H H F F H OCF ₃ F H F F CH ₃ OCF ₃ F H F F C ₂ H ₅ OCF ₃ F H F F nC ₃ H ₇ OCF ₃ F H F F K 121 N 205.2 I; Δε = 37.7; Δn = 0.1634 nC ₄ H ₉ OCF ₃ F H F F nc ₅ H ₁₁ OCF ₃ F H F F nc ₆ H ₁₃ OCF ₃ F H F F H OCF ₃ F F F F CH ₃ OCF ₃ F F F F C ₂ H ₅ OCF ₃ F F F F nC ₃ H ₇ OCF ₃ F F F F K 128 N 201.2 I; Δε = 43.8; Δn = 0.1411 nC ₄ H ₉ OCF ₃ F F F F nc ₅ H ₁₁ OCF ₃ F F F F nc ₆ H ₁₃ OCF ₃ F F F F H OCHF ₂ H H F F CH ₃ OCHF ₂ H H F F C ₂ H ₅ OCHF ₂ H H F F nC ₃ H ₇ OCHF ₂ H H F F nC ₄ H ₉ OCHF ₂ H H F F nc ₅ H ₁₁ OCHF ₂ H H F F nc ₆ H ₁₃ OCHF ₂ H H F F H OCHF ₂ F H F F CH ₃ OCHF ₂ F H F F C ₂ H ₅ OCHF ₂ F H F F nC ₃ H ₇ OCHF ₂ F H F F nC ₄ H ₉ OCHF ₂ F H F F nc ₅ H ₁₁ OCHF ₂ F H F F nc ₆ H ₁₃ OCHF ₂ F H F F H OCHF ₂ F F F F CH ₃ OCHF ₂ F F F F C ₂ H ₅ OCHF ₂ F F F F nC ₃ H ₇ OCHF ₂ F F F F nC ₄ H ₉ OCHF ₂ F F F F nc ₅ H ₁₁ OCHF ₂ F F F F nc ₆ H ₁₃ OCHF ₂ F F F F H OCHFCF ₃ H H F F CH ₃ OCHFCF ₃ H H F F C ₂ H ₅ OCHFCF ₃ H H F F nC ₃ H ₇ OCHFCF ₃ H H F F nC ₄ H ₉ OCHFCF ₃ H H F F nc ₅ H ₁₁ OCHFCF ₃ H H F F nc ₆ H ₁₃ OCHFCF ₃ H H F F H OCHFCF ₃ F H F F CH ₃ OCHFCF ₃ F H F F C ₂ H ₅ OCHFCF ₃ F H F F nC ₃ H ₇ OCHFCF ₃ F H F F nC ₄ H ₉ OCHFCF ₃ F H F F nc ₅ H ₁₁ OCHFCF ₃ F H F F nc ₆ H ₁₃ OCHFCF ₃ F H F F H OCHFCF ₃ F F F F CH ₃ OCHFCF ₃ F F F F C ₂ H ₅ OCHFCF ₃ F F F F nC ₃ H ₇ OCHFCF ₃ F F F F nC ₄ H ₉ OCHFCF ₃ F F F F nc ₅ H ₁₁ OCHFCF ₃ F F F F nc ₆ H ₁₃ OCHFCF ₃ F F F F H OCHFCF ₃ H H F F CH ₃ OCHFCF ₃ H H F F C ₂ H ₅ OCHFCF ₃ H H F F nC ₃ H ₇ OCHFCF ₃ H H F F nC ₄ H ₉ OCHFCF ₃ H H F F nc ₅ H ₁₁ OCHFCF ₃ H H F F nc ₆ H ₁₃ OCHFCF ₃ H H F F H OCHFCF ₃ F H F F CH ₃ OCHFCF ₃ F H F F C ₂ H ₅ OCHFCF ₃ F H F F nC ₃ H ₇ OCHFCF ₃ F H F F nC ₄ H ₉ OCHFCF ₃ F H F F nc ₅ H ₁₁ OCHFCF ₃ F H F F nc ₆ H ₁₃ OCHFCF ₃ F H F F H OCHFCF ₃ F F F F CH ₃ OCHFCF ₃ F F F F C ₂ H ₅ OCHFCF ₃ F F F F nC ₃ H ₇ OCHFCF ₃ F F F F nC ₄ H ₉ OCHFCF ₃ F F F F nc ₅ H ₁₁ OCHFCF ₃ F F F F nc ₆ H ₁₃ OCHFCF ₃ F F F F H OCF ₂ CHFCF ₃ H H F F CH ₃ OCF ₂ CHFCF ₃ H H F F C ₂ H ₅ OCF ₂ CHFCF ₃ H H F F nC ₃ H ₇ OCF ₂ CHFCF ₃ H H F F nC ₄ H ₉ OCF ₂ CHFCF ₃ H H F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ H H F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ H H F F H OCF ₂ CHFCF ₃ F H F F CH ₃ OCF ₂ CHFCF ₃ F H F F C ₂ H ₅ OCF ₂ CHFCF ₃ F H F F nC ₃ H ₇ OCF ₂ CHFCF ₃ F H F F nC ₄ H ₉ OCF ₂ CHFCF ₃ F H F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F H F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F H F F H OCF ₂ CHFCF ₃ F F F F CH ₃ OCF ₂ CHFCF ₃ F F F F C ₂ H ₅ OCF ₂ CHFCF ₃ F F F F nC ₃ H ₇ OCF ₂ CHFCF ₃ F F F F nC ₄ H ₉ OCF ₂ CHFCF ₃ F F F F nc ₅ H ₁₁ OCF ₂ CHFCF ₃ F F F F nc ₆ H ₁₃ OCF ₂ CHFCF ₃ F F F F H NCS H H F F CH ₃ NCS H H F F C ₂ H ₅ NCS H H F F nC ₃ H ₇ NCS H H F F nC ₄ H ₉ NCS H H F F nc ₅ H ₁₁ NCS H H F F nc ₆ H ₁₃ NCS H H F F H NCS F H F F CH ₃ NCS F H F F C ₂ H ₅ NCS F H F F nC ₃ H ₇ NCS F H F F nC ₄ H ₉ NCS F H F F nc ₅ H ₁₁ NCS F H F F nc ₆ H ₁₃ NCS F H F F H NCS F F F F CH ₃ NCS F F F F C ₂ H ₅ NCS F F F F nC ₃ H ₇ NCS F F F F nC ₄ H ₉ NCS F F F F nc ₅ H ₁₁ NCS F F F F nc ₆ H ₁₃ NCS F F F F H C ₂ F ₅ H H F F CH ₃ C ₂ F ₅ H H F F C ₂ H ₅ C ₂ F ₅ H H F F nC ₃ H ₇ C ₂ F ₅ H H F F nC ₄ H ₉ C ₂ F ₅ H H F F nc ₅ H ₁₁ C ₂ F ₅ H H F F nc ₆ H ₁₃ C ₂ F ₅ H H F F H C ₂ F ₅ F H F F CH ₃ C ₂ F _s F H F F C ₂ H ₅ C ₂ F ₅ F H F F nC ₃ H ₇ C ₂ F ₅ F H F F nC ₄ H ₉ C ₂ F ₅ F H F F nc ₅ H ₁₁ C ₂ F ₅ F H F F nc ₆ H ₁₃ C ₂ F ₅ F H F F H C ₂ F ₅ F F F F CH ₃ C ₂ F ₅ F F F F C ₂ H ₅ C ₂ F ₅ F F F F nC ₃ H ₇ C ₂ F ₅ F F F F nC ₄ H ₉ C ₂ F ₅ F F F F nc ₅ H ₁₁ C ₂ F ₅ F F F F nc ₆ H ₁₃ C ₂ F ₅ F F F F H C ₃ F ₇ H H F F CH ₃ C ₃ F ₇ H H F F C ₂ H ₅ C ₃ F ₇ H H F F nC ₃ H ₇ C ₃ F ₇ H H F F nC ₄ H ₉ C ₃ F ₇ H H F F nc ₅ H ₁₁ C ₃ F ₇ H H F F nc ₅ H ₁₃ C ₃ F ₇ H H F F H C ₃ F ₇ F H F F CH ₃ C ₃ F ₇ F H F F C ₂ H ₅ C ₃ F ₇ F H F F nC ₃ H ₇ C ₃ F ₇ F H F F nC ₄ H ₉ C ₃ F ₇ F H F F nc ₅ H ₁₁ C ₃ F ₇ F H F F nc ₆ H ₁₃ C ₃ F ₇ F H F F H C ₃ F ₇ F F F F CH ₃ C ₃ F ₇ F F F F C ₂ H ₅ C ₃ F ₇ F F F F nC ₃ H ₇ C ₃ F ₇ F F F F nC ₄ H ₉ C ₃ F ₇ F F F F nc ₅ H ₁₁ C ₃ F ₇ F F F F nc ₆ H ₁₃ C ₃ F ₇ F F F F H SF ₅ H H F F CH ₃ SF ₅ H H F F C ₂ H ₅ SF ₅ H H F F nC ₃ H ₇ SF ₅ H H F F nC ₄ H ₉ SF ₅ H H F F nc ₅ H ₁₁ SF ₅ H H F F nc ₆ H ₁₃ SF ₅ H H F F H SF ₅ F H F F CH ₃ SF ₅ F H F F C ₂ H ₅ SF ₅ F H F F nC ₃ H ₇ SF ₅ F H F F nC ₄ H ₉ SF ₅ F H F F nc ₅ H ₁₁ SF ₅ F H F F nc ₆ H ₁₃ SF ₅ F H F F H SF ₅ F F F F CH ₃ SF ₅ F F F F C ₂ H ₅ SF ₅ F F F F nC ₃ H ₇ SF ₅ F F F F nC ₄ H ₉ SF ₅ F F F F nc ₅ H ₁₁ SF ₅ F F F F nc ₆ H ₁₃ SF ₅ F F F F H CN H HF F CH ₃ CN H H F F C ₂ H ₅ CN H H F F nC ₃ H ₇ CN H H F F nC ₄ H ₉ CN H H F F nc ₅ H ₁₁ CN H H F F nc ₆ H ₁₃ CN H H F F H CN F H F F CH ₃ CN F H F F C ₂ H ₅ CN F H F F nC ₃ H ₇ CN F H F F nC ₄ H ₉ CN F H F F nc ₅ H ₁₁ CN F H F F nc ₆ H ₁₃ CN F H F F H CN F F F F CH ₃ CN F F F F C ₂ H ₅ CN F F F F nC ₃ H ₇ CN F F F F nC ₄ H ₉ CN F F F F nc ₅ H ₁₁ CN F F F F nc ₆ H ₁₃ CN F F F F H CF ₃ H H F F C ₂ H ₅ CF ₃ H H F F nC ₃ H ₇ CF ₃ H H F F nC ₄ H ₉ CF ₃ H H F F nc ₅ H ₁₁ CF ₃ H H F F nc ₆ H ₁₃ CF ₃ H H F F CH ₂ = CH CF ₃ H H F F H CF ₃ F F F F C ₂ H ₅ CF ₃ F F F F nC ₃ H ₇ CF ₃ F F F F nC ₄ H ₉ CF ₃ F F F F nc ₅ H ₁₁ CF ₃ F F F F nc ₆ H ₁₃ CF ₃ F F F F CH ₂ = CH CF ₃ F F F F H F H H F F C ₂ H ₅ F H H F F nC ₃ H ₇ F H H F F nC ₄ H ₉ F H H F F nc ₅ H ₁₁ F H H F F nc ₆ H ₁₃ F H H F F CH ₂ = CH F H H F F

Example 6

Enantiomer separation of

8.7 g of T are added for enantiomer separation via a preparative Enantio HPLC column. After obtaining the two fractions is recrystallized in each case from ethanol and determines the rotation value.
3.18 g Enantio-HPLC: 99.68% - rotation value: + 29.0 °
3.74 g Enantio-HPLC: 98.25% - rotation value: -28.0 °

Enantio-HPLC: 99,97 % - Drehwert: +32,0° Enantio-HPLC: 99,40 % - Drehwert: -32,1°

Enantio-HPLC: 100,0 % - Drehwert: +4,5° Enantio-HPLC: 99,9 % - Drehwert: -4,9 °

Enantio-HPLC- 99,98 % - Drehwert: +28,5° Enantio-HPLC: 100,00 % - Drehwert: -31,4° Analogously, the following racemates are separated into the enantiomers:

Enantio-HPLC: 99.97% - rotation value: + 32.0 ° Enantio-HPLC: 99.40% - rotation: -32.1 °

Enantio-HPLC: 100.0% - rotation value: + 4.5 ° Enantio-HPLC: 99.9% - rotation: -4.9 °

Enantio-HPLC- 99.98% - rotation value: + 28.5 ° Enantio-HPLC: 100.00% - rotation: -31.4 °

Examples mix Example M1

CCH-5CF ₃ 3.00% Clearing point [° C]: +80.0 CCP 1F.F.F 3.00% Δn [589 nm, 20 ° C]: +0.0660 CCP 2F.F.F 8.00% Δε [kHz, 20 ° C]: +10.4 CCP 3F.F.F 8.00% d · Δn [20 ° C, μm]: 0.50 CCP 5F.F.F 5.00% Twist [°]: 90 CCP-20CF ₃ .F 8.00% V ₁₀ [V]: 1.31 CCP-50CF ₃ .F 8.00% CCOC-3-3 2.00% CCOC-4-3 2.00% CCQU-2-F 10.00% CCQU-3-F 12.00% CCQU-5-F 8.00% ACQU-3-F 15.00% CCH 301 3.00% CCH 501 5.00%

Example M2

CCH 501 7.00% Clearing point [° C]: + 88,5- CCH-5CF ₃ 7.00% Δn [589 nm, 20 ° C]: +0.0657 CCP 2F.F.F 4.00% Δε [kHz, 20 ° C]: +9.9 CCP 3F.F.F 7.00% d · Δn [20 ° C, μm]: 0.50 CCP 5F.F.F 5.00% Twist [°]: 90 CCP-30CF ₃ .F 8.00% V ₁₀ [V]: 1.45 CCP-50CF ₃ .F 8.00% CCOC-3-3 3.00% CCOC-3-5 2.00% CCOC-4-3 4.00% CCQU-2-F 10.00% CCQU-3-F 12.00% CCQU-5-F 8.00% ACQU-3-F 15.00%

Example M3

CCH 301 7.00% Clearing point [° C]: +81.0 CCH 501 10.00% Δn [589 nm, 20 ° C]: +0.0608 CCH-5CF ₃ 2.00% Δε [kHz, 20 ° C]: +8.4 CCP 2F.F.F 9.00% d · Δn [20 ° C, μm]: 0.50 CCP 3F.F.F 4.00% Twist [°]: 90 CCP 5F.F.F 4.00% V ₁₀ [V]: 1.49 CCP-30CF ₃ .F 2.00% CCP-50CF ₃ .F 4.00% CCOC-3-3 3.00% CCOC-3-5 2.00% CCOC-4-3 4.00% ACQU-3-F 15.00% CCQU-2-F 10.00% CCQU-3-F 12.00% CCQU-5-F 8.00% CCH-35 4.00%

Example M4

CCP-1 F.F.F 4.00% Clearing point [° C]: +79.0 CCP 2F.F.F 10.00% Δn [589 nm, 20 ° C]: +0.0808 CCP 3F.F.F 9.00% Δε [kHz, 20 ° C]: +15.5 CCP 5F.F.F 5.00% d · Δn [20 ° C, μm]: 0.50 CCP-30CF ₃ .F 5.00% Twist [°]: 90 CCP-50CF ₃ .F 7.00% γ ₁ [20 ° C, mPa.s]: 150 PUQU-2-F 5.00% V ₁₀ [V]: 0.98 PUQU-3-F 5.00% CCQU-2-F 11.00%. CCQU-3-F 12.00% CCQU-5-F 8.00% CCGU-3-F 4.00% ACQU-3-F 15.00%

Example M5

BCH 3F.F 10.80% Clearing point [° C]: +89.0 BCH 5F.F 9.00% Δn [589 nm, 20 ° C]: +0.0930 ECCP-30CF ₃ 4.50% Δε [kHz, 20 ° C]: +6.2 ECCP-50CF ₃ 4.50% CBC 33F 1.80% CBC-53F 1.80% CBC-55F 1.80% PCH-6F 7.20% PCH-7F 5.40% CCP-20CF ₃ 7.20% CCP-30CF ₃ 10.80% CCP-40CF ₃ 6.30% CCP-50CF ₃ 9.90% PCH-5F 9.00% ACQU-3-F 10.00%

Example M6

CCH-35 3.00% Clearing point [° C]: +81.0 CC-3-V1 4.00% Δn [589 nm, 20 ° C]: +0.0912 CCP-1 F.F.F 10.00% d · Δn [20 ° C, μm]: 0.50 CCP 2F.F.F 9.00% Twist [°]: 90 CCP 3F.F.F 9.00% γ ₁ [20 ° C, mPa.s]: 129 CCP-20CF ₃ .F 6.00% V ₁₀ [V]: 1.30 CCG V F 9.00% CCP-20CF ₃ 8.00% CCP-30CF ₃ 8.00% CCP-40CF ₃ 6.00% CCP-50CF ₃ 7.00% PUQU-2-F 5.00% PUQU-3-F 7.00% APUQU-2-F 4.50% CGUQU-3-F 3.50% CBC 33 1.00%

Example M7

CCP 2F.F.F 11.00% Clearing point [° C]: +80.0 CCP-20CF ₃ 7.00% Δn [589 nm, 20 ° C]: +0.1034 CCP-30CF ₃ 8.00% d · Δn [20 ° C, μm]: 0.50 CCP-40CF ₃ 5.00% Twist [°]: 90 PGU-2-F 8.00% V ₁₀ [V]: 1.22 PGU-3-F 7.00% CC-3-V1 10.00% CCH-35 3.00% CCP-V-1 5.00% CCP-20CF ₃ .F 8.00% CCP-30CF ₃ .F 11.00% PUQU-2-F 4.00% PUQU-3-F 6.00% ACQU-3-F 7.00%

Example M8

CCP-1 F.F.F 6.00% S → N [° C]: -40,0 CCP 2F.F.F 10.00% Clearing point [° C]: +80.0 CCP-20CF ₃ 8.00% Δn [589 nm, 20 ° C]: +0.1029 CCP-30CF ₃ 8.00% d · Δn [20 ° C, μm]: 0.50 CCP-40CF ₃ 6.00% Twist [°]: 90 CCP-50CF ₃ 8.00% V ₁₀ [V]: 1.24 PGU-2-F 8.00% PGU-3-F 7.00% CC-3-V1 8.00% CCH-35 5.00% CCP-V-1 5.00% CCP-30CF ₃ .F 3.00% PUQU-2-F 4.00% PUQU-3-F 6.00% ACQU-3-F 8.00%

Example M9

CC-3-V1 5.00% S → N [° C]: -30.0 CCP-1 F.F.F 5.00% Clearing point [° C]: +85.5 CCP 2F.F.F 8.00% Δn [589 nm, 20 ° C]: +0.0931 CCP-20CF ₃ .F 8.00% Δε [kHz, 20 ° C]: 12.1 CCP-20CF ₃ 5.00% γ ₁ [20 ° C, mPa.s]: 135 CCP-30CF ₃ 8.00% d · Δn [20 ° C, μm]: 0.50 CCP-40CF ₃ 6.00% Twist [°]: 90 CCP-50CF ₃ 8.00% V ₁₀ [V]: 1.23 PUQU-2-F 5.00% PUQU-3-F 7.00% PGU-2-F 5.00% CCP-V-1 10.00% ACQU-3-F 12.00% ACQU-4-F 8.00%

Example M10

CC-3-V1 6.00% S → N [° C]: -40,0 CCP-1 F.F.F 6.00% Clearing point [° C]: +83.5 CCP 2F.F.F 7.00% Δn [589 nm, 20 ° C]: +0.0917 CCP-20CF ₃ .F 10.00% Δε [kHz, 20 ° C]: 11.7 CCP-20CF ₃ 8.00% γ ₁ [20 ° C, mPa.s]: 125 CCP-30CF ₃ 8.00% d · Δn [20 ° C, μm]: 0.50 CCP-40CF ₃ 6.00% Twist [°]: 90 CCP-50CF ₃ 4.00% V ₁₀ [V]: 1.25 PUQU-2-F 5.00% PUQU-3-F 8.00% PGU-2-F 4.00% CCP-V-1 10.00% ACQU-3-F 10.00% ACQU-4-F 8.00%

Example M11 (IPS)

CDU-2-F 5.00% Clearing point [° C]: +81 PGU-2-F 2.50% Δn [589 nm, 20 ° C]: +0.0850 CCZU-2-F 4.00% Δε [kHz, 20 ° C]: 10.1 CCZU-3-F 11.00% γ ₁ [20 ° C, mPa.s]: 98 CCP-V-1 15.00% CCQU-3-F 10.00% PUQU-2-F 4.00% PUQU-3-F 5.00% CC-3-V1 11.00% PCH-302 3.50% CC-5-V 11.00% ACQU-3-F 9.00% ACQU-4-F 9.00%

Example M12 (IPS)

PGU-2-F 9.00% Clearing point [° C]: 81.0 PGU-3-F 2.00% Δn [589 nm, 20 ° C]: .1090 CGZP-2-OT 8.00% Δε [kHz, 20 ° C]: 11.0 CGZP-3-OT 10.00% γ ₁ [20 ° C, mPa.s]: 100 CCP-20CF ₃ 6.00% CCP-30CF ₃ 6.50% PUQU-2-F 4.00% PUQU-3-F 3.50% CCP-V-1 9.00% CC-3-V1 11.00% PCH-302 15.00% ACQU-3-F 8.00% ACQU-4-F 8.00%

Example M13

CC-4-V 17.00% Clearing point [° C]: 74.5 CC-3-V1 3.00% Δn [589 nm, 20 ° C]: +0.0890 CCQU-2-F 12.00% Δε [kHz, 20 ° C]: 12.7 CCQU-3-F 12.00% γ ₁ [20 ° C, mPa.s]: 119 CCQU-5-F 10.00% V ₁₀ [V]: 1.09 CCP-20CF ₃ 5.00% PGU-2-F 3.00% PGU-3-F 6.00% AUUQGU-3-F 8.00% CCP-1 F.F.F 8.00% CCP 3F.F.F 9.00% BCH 3F.F.F 7.00%

Example M14

CC-3-V1 6.00% S → N [° C]: <-40,0 CCP-1 F.F.F 9.00% Clearing point [° C]: 83.5 CCP 2F.F.F 9.00% Δn [589 nm, 20 ° C]: 0.0941 CCP 3F.F.F 10.00% Δε [kHz, 20 ° C]: 11.4 CCQU-3-F 11.00% γ ₁ [20 ° C, mPa.s]: 137 CCQU-5-F 9.00% V ₁₀ [V]: 1.23 CCP-20CF ₃ 6.00% CCP-30CF ₃ 8.00% CCP-50CF ₃ 2.00% CGU-2-F 4.00% PGU-2-F 6.00% PGU-3-F 6.00% CCP-V-1 7.00% ACQU-3-F 7.00%

Example M15

CC-3-V1 5.00% S → N [° C]: <-40,0 CCP-1 F.F.F 7.00% Clearing point [° C]: 84.0 CCP 2F.F.F 10.00% Δn [589 nm, 20 ° C]: .0919 ACQU-1-F 8.00% Δε [kHz, 20 ° C]: 11.9 ACQU-3-F 8.00% γ ₁ [20 ° C, mPa.s]: 135 CCG V F 11.00% V ₁₀ [V]: 1.19 BCH 3F.F 2.50% CCP-20CF ₃ 8.00% CCP-30CF ₃ 8.00% CCP-40CF ₃ 5.00% CCP-V-1 8.00% PUQU-2-F 5.50% PUQU-3-F 8.00% CCGU-3-F 6.00%

Example M16

CC-3-V1 5.00% CCP-1 F.F.F 7.00% CCP 2F.F.F 6.00% CCQU-3-F 10.00% CCG V F 6.00% CCP-20CF ₃ 8.00% CCP-30CF ₃ 8.00% CCP-40CF ₃ 6.00% CCP-50CF ₃ 8.00% ACQU-2-F 6.00% ACQU-3-F 6.00% PUQU-2-F 5.00% PUQU-3-F 7.00% PGU-3-F 6.00% CCP-V-1 6.00%

Example M17

CCP-20CF ₃ 8.00% S → N [° C]: <-30,0 CCP-30CF ₃ 8.00% Clearing point [° C]: 75.0 CCP-40CF ₃ 5.00% Δn [589 nm, 20 ° C]: .0858 PGU-2-F 5.00% Δε [kHz, 20 ° C]: 13.3 PGU-3-F 5.00% γ ₁ [20 ° C, mPa-s]: 152 CCP-1 F.F.F 10.00% V ₁₀ [V]: 1.07 CCP 2F.F.F 11.00% CCP 3F.F.F 12.00% CCZU-2-F 3.00% CCZU-3-F 13.00% ACQU-2-F 8.00% ACQU-3-F 8.00% ACQU-5-F 4.00%

Example M18

CC-4-V 11.00% S → N [° C]: <-40,0 CDU-2-F 7.00% Clearing point [° C]: 76.5 CDU-3-F 8.00% Δn [589 nm, 20 ° C]: .0870 CDU-5-F 9.00% Δε [kHz, 20 ° C]: 13.6 CCP 1F.F.F 8.50% γ ₁ [20 ° C, mPa.s]: 146 CCP-20CF ₃ 8.00% V ₁₀ [V]: 1.09 CCP-30CF ₃ 6.50% PGU-2-F 3.00% PGU-3-F 6.00% CCGU-3-F 6.00% CBC 33 3.00% ACQU-2-F 8.00% ACQU-3-F 8.00% ACQU-5-F 8.00%

Example M19

CC-4-V 10.00% S → N [° C]: <-40,0 CCP-1 F.F.F 9.00% Clearing point [° C]: 75.0 CCP 2F.F.F 9.00% Δn [589 nm, 20 ° C]: .0869 CCP-30CF ₃ .F 8.00% Δε [kHz, 20 ° C]: 13.1 CCP-20CF ₃ 8.00% γ ₁ [20 ° C, mPa.s]: 128 CCP-30CF ₃ 8.00% V ₁₀ [V]: 1.06 ACQU-2-F 8.00% ACQU-3-F 8.00% ACQU-4-F 8.00% PGU-2-F 2.00% PUQU-2-F 5.00% PUQU-3-F 8.00% CCGU-3-F 6.00% CBC 33 3.00%

Example M20

CC-4-V 18.00% S → N [° C]: <-40,0 CC-3-V1 3.00% Clearing point [° C]: 75.0 CCQU-2-F 11.00% Δn [589 nm, 20 ° C]: 0.0891 CCQU-3-F 12.00% Δε [kHz, 20 ° C]: 13.0 CCQU-5-F 8.00% γ ₁ [20 ° C, mPa.s]: 113 CCP-20CF ₃ 8.00% V ₁₀ [V]: 1.08 PGU-2-F 2.00% PGU-3-F 6.00% APUQU-2-F 8.00% APUQU-3-F 9.00% CCP 1F.F.F 7.00% CCP 2F.F.F 7.00% CCGU-3-F 1.00%

Example M21

CC-4-V 17.00% S → N [° C]: <-40,0 PUQU-2-F 5.00% Clearing point [° C]: 75.5 PUQU-3-F 7.00% Δn [589 nm, 20 ° C]: 0.0894 CCP-20CF ₃ 6.00% Δε [kHz, 20 ° C]: 14.0 CCP-30CF ₃ 5.00% γ ₁ [20 ° C, mPa.s]: 120 CCP 2F.F.F 5.00% V ₁₀ [V]: 1.06 CCZU-2-F 3.00% CCZU-3-F 13.00% PGU-3-F 6.00% ACQU-1-F 8.00% ACQU-3-F 8.00% ACQU-4-F 8.00% CCGU-3-F 6.00% CBC 33 3.00%

Example M22

CC-4-V 16.00% S → N [° C]: <-40,0 CC-3-V1 8.00% Clearing point [° C]: 75.5 CCP-1 F.F.F 5.00% Δn [589 nm, 20 ° C]: 0.0916 CCP 2F.F.F 6.00% Δε [kHz, 20 ° C]: 13.6 CCQU-2-F 10.00% γ ₁ [20 ° C, mPa.s]: 107 CCQU-3-F 12.00% V ₁₀ [V]: 1.08 CCP-20CF ₃ 4.00% CCZU-3-F 13.00% PGU-2-F 5.00% PGU-3-F 5.00% APUQU-2-F 8.00% APUQU-3-F 8.00%

Example M23

CCP-1 F.F.F 6.00% Clearing point [° C]: 78.2 CCP 2F.F.F 9.00% Δn [589 nm, 20 ° C]: 0.0791 CCP 3F.F.F 6.00% Δε [kHz, 20 ° C]: 14.3 CCP 5F.F.F 4.00% CCP-20CF ₃ .F 5.00% CCP-30CF ₃ .F 5.00% CCP-50CF ₃ .F 7.00% CDU-2-F 7.00% CDU-3-F 10.00% CDU-5-F 10.00% CGU-3-F 4.00% CCGU-3-F 9.00% ACQU-3-F 18.00%

Example M24

CCQU-2-F 13.00% Clearing point [° C]: 84.5 CCQU-3-F 14.00% Δn [589 nm, 20 ° C]: 0.0779 CCQU-5-F 13.00% Δε [kHz, 20 ° C]: 18.7 ACQU-5-F 33.00% γ ₁ [20 ° C, mPa.s]: 182 APUQU-2-F 7.00% V ₁₀ [M]: 0.95 APUQU-3-F 9.00% CC-4-V 11.00%

Example M25

CC-4-V 18.00% Clearing point [° C]: 74.5 CC-3-V1 5.00% Δn [589 nm, 20 ° C]: .0882 CCP- ₂ FFF 8.00% Δε [kHz, 20 ° C]: 12.9 CCQU-2-F 9.00% γ ₁ [20 ° C, mPa.s]: 103 CCQU-3-F 11.00% V ₁₀ [V]: 1.09 CCQU-5-F 11.00% CCQG-3-F 6.00% BCH 3F.F.F 8.00% APUQU-2-F 6.00% APUQU-3-F 6.00% PUQU-2-F 3.00% PUQU-3-F 6.00% CCGU-3-F 1.50% PGP-2-3 1.50%

Example M26 (IPS)

CCP-20CF ₃ 7.00% Clearing point [° C]: 80.0 CCP-30CF ₃ 7.00% Δn [589 nm, 20 ° C]: .1102 CCP-40CF ₃ 7.00% Δε [kHz, 20 ° C]: 11.1 CCP-50CF ₃ 3.50% γ ₁ [20 ° C, mPa.s]: 82 CCZU-3-F 5.00% V ₁₀ [V]: 1.13 PGU-2-F 9.00% PGU-3-F 8.00% PUQU-2-F 6.00% PUQU-3-F 6.00% CC-3-V1 13.00% CC-4-V 14.00% CCP-V-1 8.00% APUQU-2-F 6.50%

Example M27 (IPS)

CCP-20CF ₃ 8.00% Clearing point [° C]: 79.5 CCP-30CF ₃ 8.00% Δn [589 nm, 20 ° C]: .1095 CCP-40CF ₃ 8.00% Δε [kHz, 20 ° C]: 11.4 CCZU-3-F 5.00% γ ₁ [20 ° C, mPa.s]: 87 PGU-2-F 9.00% V ₁₀ [V]: 1.11 PGU-3-F 8.50% PUQU-2-F 6.00% PUQU-3-F 5.00% CC-3-V1 12.50% CC-4-V 14.00% CCP-V-1 9.00% AGUQU-2-F 3.50% AGUQU-3-F 3.50%

Example M28 (IPS)

CCP 2F.F.F 6.50% Clearing point [° C]: 78.0 CCP-30CF ₃ 6.00% Δn [589 nm, 20 ° C]: .0805 CCZU-2-F 4.00% Δε [kHz, 20 ° C]: 14.8 CCZU-3-F 15.00% γ ₁ [20 ° C, mPa.s]: 121 CDU-2-F 9.00% CDU-3-F 4.00% CCQU-3-F 13.00% CCQU-5-F 10.00% PUQU-2-F 5.00% PUQU-3-F 5.00% APUQU-2-F 6.00% CC-3-V1 12.00% CC-4-V 4, 50%

Example 28 (IPS)

CDU-2-F 9.00% Clearing point [° C]: 76.5 CDU-3-F 8.00% Δn [589 nm, 20 ° C]: 0.0960 PGU-2-F 9.00% Δε [kHz, 20 ° C]: 12.7 CCZU-2-F 4.00% γ ₁ [20 ° C, mPa.s]: 92 CCZU-3-F 11.00% V ₁₀ [V]: 1.02 PUQU-2-F 4.00% PUQU-3-F 6.00% APUQU-2-F 7.00% CCP-V-1 14.50% CC-3-V1 12.50% CC-4-V 10.00% CCH-35 5.00%

Example M30 (IPS)

CCP-30CF ₃ 3.50% Clearing point [° C]: 75.5 CDU-2-F 5.00% Δn [589 nm, 20 ° C]:. 0.0975 PGU-2-F 6.50% Δε [kHz, 20 ° C]: 8.4 PUQU-2-F 8.00% γ ₁ [20 ° C, mPa.s]: 67 PUQU-3-F 8.00% V ₁₀ [V]: 1.28 CCP-V-1 13.00% CCP-V2-1 9.50% CC-3-V1 13.00% CC-5-V 9.00% CC-4-V 14.00% PCH-302 3.50% APUQU-2-F 7.00%

Example M31 (IPS)

PGU-2-F 6.50% Clearing point [° C]: 74.0 CDU-2-F 9.00% Δn [589 nm, 20 ° C]: .1005 PUQU-2-F 11.00% Δε [kHz, 20 ° C]: 14.1 PUQU-3-F 10.00% γ ₁ [20 ° C, mPa.s]: 92 CCP-30CF ₃ 8.00% CCZU-3-F 11.50% CC-4-V 10.00% CC-5-V 3.00% CC-3-V1 11.00% CCP-V2-1 13.00% APUQU-2-F 7.00%

Example M32

CCQU-2-F 10.00% Clearing point [° C]: 82.0 CCQU-3-F 12.00% Δn [589 nm, 20 ° C]: 0.0792 CCQU-5-F 8.00% Δε [kHz, 20 ° C]: 11.2 CCP-1 F.F, F 6.00% V ₁₀ [V]: 1.20 CCP 2F.F.F 5.00% CCP 3F.F.F 5.00% CC-3-V1 10.00% CC-4-V 14.00% CGU-2-F 5.00% CCGU-3-F 5.00% ACQG-3-F 5.00% ACQG-4-F 5.00% APUQU-2-F 5.00% APUQU-3-F 5.00%

Example M33

CCQU-2-F 11.00% Clearing point [° C]: 81.5 CCQU-3-F 13.00% Δn [589 nm, 20 ° C]: .0804 CCQU-5-F 11.00% Δε [kHz, 20 ° C]: 13.6 CCP-1 F.F.F 8.00% γ ₁ [20 ° C, mPa.s]: 153 CCP 2F.F.F 10.00% V ₁₀ [V]: 1.06 CCP 3F.F.F 10.00% CCP 5F.F.F 6.00% CC-3-V1 9.00% CGU-3-F 4.00% ACQG-3-F 3.00% ACQG-4-F 5.00% APUQU-2-F 5.00% APUQU-3-F 5.00%

Example M34

CCH-5CF ₃ 5.00% Clearing point [° C]: 80.5 CCP-1 F.F.F 5.00% Δn [589 nm, 20 ° C]: 0.0660 CCP 2F.F.F 9.00% Δε [kHz, 20 ° C]: 9.7 CCP 3F.F.F 8.00% V ₁₀ [V]: 1.27 CCP 5F.F.F 5.00% CCP-20CF ₃ .F 6.00% CCP-50CF ₃ .F 6.00% CCOC-3-3 2.00% CCOC-4-3 2.00% CCQU-2-F 10.00% CCQU-3-F 12.00% CCQU-5-F 8.00% CCH 501 6.00% ACQG-3-F 8.00% ACQG-4-F 8.00%

Example M35

CCP-1 F.F.F 7.00% Clearing point [° C]: 81.5 CCP 2F.F.F 8.00% Δn [589 nm, 20 ° C]: 0.0658 CCP 3F.F.F 7.00% Δε [kHz, 20 ° C]: 13.5 CCP 5F.F.F 4.00% V ₁₀ [V]: 1.06 CCQU-2-F 11.00% CCQU-3-F 12.00% CCQU-5-F 8.00% ACQU-2-F 8.00% ACQU-3-F 9.00% ACQU-5-F 8.00% ACQG-3-F 7.00% ACQG-4-F 5.00% CCOC-3-3 3.00% CCOC-4-3 3.00%

Example M36

AUUQU-3-F 6.00% Clearing point [° C]: 98.0 AGUQU-3-F 6.00% Δn [589 nm, 20 ° C]: .0927 APUQU-2-F 6.00% Δε [kHz, 20 ° C]: 18.9 CGU-2-F 5.00% CGU-3-F 5.00% CGU-5-F 5.00% CCZU-2-F 5.50% CCZU-3-F 10.50% CCZU-5-F 5.50% CCQU-2-F 10.00% CCQU-3-F 10.00% CCQU-5-F 10.00% CC-5-V 9.50% CCPC-33 2.00% CCPC-34 2.00% CCPC-35 2.00%

Example M37

CCQU-2-F 7.00% Clearing point [° C]: 85.5 CCQU-3-F 8.00% Δn [589 nm, 20 ° C]: .0783 CCQU-5-F 8.00% Δε [kHz, 20 ° C]: 11.66 CCQG-3-F 6.00% γ ₁ [20 ° C, mPa.s]: 213 ACQU-2-F 17.00% V ₁₀ [V]: 0.90 ACQU-5-F 16.00% PUQU-2-F 5.00% PUQU-3-F 5.00% CCGU-3-F 5.00% CCOC-4-3 3.00% CCZU-2-F 3.00% CCZU-3-F 14.00% CCZU-5-F 3.00%

Example M38

BCH 3F.F 10.80% Clearing point [° C]: 56.9 BCH 5F.F 9.00% Δn [589 nm, 20 ° C]: .0834 ECCP-30CF ₃ 4.50% Δε [kHz, 20 ° C]: 4.1 ECCP-50CF ₃ 4.50% γ ₁ [20 ° C, mPa.s]: 65 CBC 33F 1.80% CBC-53F 1.80% CBC-55F 1.80% PCH-6F 7.20% PCH-7F 5.40% CCP-20CF ₃ 7.20% CCP-30CF ₃ 10.80% CCP-40CF ₃ 6.30% CCP-50CF ₃ 9.90% PCH-5F 9.00% AUUQPU-3-F 10.00%

Example M39

CCP-1 F.F.F 3.00% Clearing point [° C]: 79.5 CCP 2F.F.F 6.00% Δn [589 nm, 20 ° C]: 0.0796 CCP 3F.F.F 7.00% Δε [kHz, 20 ° C]: 10.12 CCP 5F.F.F 5.00% γ ₁ [20 ° C, mPa.s]: 202 CCQU-2-F 11.00% V ₁₀ [V]: 0.93 CCQU-3-F 12.00% CCQU-5-F 8.00% CGU-2-F 4.00% CGU-3-F 7.00% CCGU-3-F 9.00% ACQU-2-F 8.00% ACQU-3-F 10.00% ACQU-4-F 10.00%

Example M40

CCH-5CF ₃ 2.00% Clearing point [° C]: 79.5 CCP 2F.F.F 9.00% Δn [589 nm, 20 ° C]: .0659 CCP 3F.F.F 7.00% Δε [kHz, 20 ° C]: 8.22 CCP 5F.F.F 4.00% γ ₁ [20 ° C, mPa.s]: 169 CCP-20CF ₃ .F 7.00% V ₁₀ [V]: 1.14 CCP-50CF ₃ .F 6.00% CCOC-3-3 2.00% CCOC-4-3 2.00% CCQU-2-F 10.00% CCQU-3-F 12.00% CCQU-5-F 8.00% ACQU-2-F 8.00% ACQU-3-F 10.00% ACQU-4-F 8.00% CCH 501 5.00%

Example M41

CCP-1 F.F.F 6.00% Clearing point [° C]: 80.0 CCP 2F.F.F 9.00% Δn [589 nm, 20 ° C]: 0.0694 CCP 3F.F.F 10.00% Δε [kHz, 20 ° C]: 8.96 CCP 5F.F.F 6.00% γ ₁ [20 ° C, mPa.s]: 175 CCP-20CF ₃ .F 4.00% V ₁₀ [V]: 1.11 CCP-50CF ₃ .F 8.00% CCQU-2-F 11.00% CCQU-3-F 12.00% CCQU-5-F 8.00% ACQU-3-F 26.00%

Example M42

CCP 1F.F.F 8.00% Clearing point [° C]: 88.0 CCP 2F.F.F 7.00% Δn [589 nm, 20 ° C]: 0.0788 CCP 3F.F.F 9.00% Δε [kHz, 20 ° C]: 8.51 CCP 5F.F.F 6.00% γ ₁ [20 ° C, mPa-s]: 192 CCP-30CF ₃ .F 9.00% V ₁₀ [V]: 1.13 CCP-50CF ₃ .F 9.00% CGU-2-F 5.00% CCGU-3-F 5.00% CCQU-2-F 11.00% CCQU-3-F 12.00% CCQU-5-F 8.00% ACQU-3-F 6.00% ACQU-4-F 5.00%

Example M43

CCP 1F.F.F 2.00% Clearing point [° C]: 81.0 CCP-20CF ₃ 8.00% Δn [589 nm, 20 ° C]: 0.0785 CCP-30CF ₃ 8.00% Δε [kHZ, 20 ° C]: 7.27 CCP-40CF ₃ 6.00% γ ₁ [20 ° C, mPa.s]: 108 CCP-50CF ₃ 8.00% V ₁₀ [V]: 1.34 CCP-20CF ₃ .F 12.00% ACQU-2-F 8.00% ACQU-3-F 8.00% ACQU-4-F 8.00% PUQU-2-F 5.00% PUQU-3-F 7.00% CC-3-V1 8.00% CC-4-V 9.00% CCOC-4-3 3.00%

Example M44

CC-3-V1 5.00% S → N [° C]: <20.0 CCP-1 F.F.F 8.00% Clearing point [° C]: 82.5 CCP 2F.F.F 10.00% At [589 nm, 20 ° C]: .0939 CCQU-2-F 10.00% Δε [kHz, 20 ° C]: 10.6 CCQU-3-F 5.00% γ ₁ [20 ° C, mPa.s]: 128 CCP-20CF ₃ 8.00% V ₁₀ [V]: 1.19 CCP-30CF ₃ 8.00% CGU-2-F 9.00% PGU-3-F 5.00% CCP-V-1 6.00% CCG V F 18.00% APUQU-3-F 8.00%

Example M45

CCP 2F.F.F 7.00% Clearing point [° C]: 88.0 CCP 3F.F.F 6.00% Δn [589 nm, 20 ° C]: 0.0720 CCP 5F.F.F 6.00% Δε [kHz, 20 ° C]: 16.1 ACQU-2-F 10.00% γ ₁ [20 ° C, mPa.s]: 210 ACQU-3-F 10.00% V ₁₀ [V]: 0.97 ACQU-5-F 11.00% CCQU-2-F 10.00% CCQU-3-F 12.00% CCQU-5-F 10.00% CCGU-3-F 5.00% CCZU-2-F 4.00% CCZU-3-F 9.00.%

Claims (10)

1. Liquid-crystalline compounds of the formula I

   

   in which

   R¹ and R² each, independently of one another, denote H, halogen, a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH₂ groups in these radicals may each, independently of one another, be replaced by -C≡C-, -CH=CH-, -O-, -CO-O- or -O-CO- in such a way that O atoms are not linked directly to one another, where one of the radicals R¹ and R² may alternatively denote CN, OCN, SCN, NCS or SF₅,

   A¹, A², A³ and A⁴ each, independently of one another, denote

   

   

   

   or

   

   Z¹, Z² and Z³ each, independently of one another, denote -CO-O-, -O-CO-, -CF₂O-, -OCF₂-, -CH₂O-, -OCH₂-, -CH₂CH₂-, -(CH₂)₄-, -C₂F₄-, -CH₂CF₂-, -CF₂CH₂-, -CF=CF-, -CH=CH-, -C≡C- or a single bond, and

   a, b and c each, independently of one another, denote 0, 1, 2 or 3, where a + b + c ≤ 3.
2. Liquid-crystalline compounds of the formula IA

   

   in which

   R¹, R², a and b have the meanings indicated in Claim 1, where a + b = 1 or 2, and

   L¹ and L² each, independently of one another, denote H or F.
3. Liquid-crystalline compounds according to Claim 1 or 2, characterised in that a = 1 and b = 0 or a=0 and b=1.
4. Liquid-crystalline compounds according to Claim 2, characterised in that L¹ denotes fluorine and L² denotes fluorine or hydrogen.
5. Liquid-crystalline compounds according to Claim 2, characterised in that L¹ and L² denote fluorine.
6. Liquid-crystalline compounds of the formulae 11 to 131

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   in which R¹ has the meanings indicated in Claim 1 and X has the meaning of R².
7. Liquid-crystalline medium comprising at least two mesogenic compounds, characterised in that it comprises at least one compound of the formula I according to Claim 1.
8. Liquid-crystalline medium according to Claim 7, characterised in that it comprises one or more compounds selected from the group consisting of the general formulae II to IX

   

   

   

   

   

   

   

   

   in which

   R⁰ denotes n-alkyl, oxaalkyl, fluoroalkyl, alkenyloxy or alkenyl, each having up to 9 C atoms,

   X⁰ denotes F, Cl, halogenated alkyl, halogenated alkenyl, halogenated alkenyloxy or halogenated alkoxy having up to 7 C atoms,

   Z⁰ denotes -CH=CH-, -C₂H₄-, -(CH₂)₄-, -C₂F₄-, -CH₂O-, -OCH₂-, -CF=CF-, -CF₂O-, -OCF₂- or -COO-,

   Y¹,Y², Y³ and Y⁴ each, independently of one another, denote H or F, and

   r denotes 0 or 1.
9. Use of the liquid-crystalline medium according to Claim 7 or 8 for electro-optical purposes.
10. Electro-optical liquid-crystal display containing a liquid-crystalline medium according to Claim 7 or 8.